KR830008992A - N-(할로메틸)아씰아미드의 제조방법 - Google Patents
N-(할로메틸)아씰아미드의 제조방법 Download PDFInfo
- Publication number
- KR830008992A KR830008992A KR1019820000388A KR820000388A KR830008992A KR 830008992 A KR830008992 A KR 830008992A KR 1019820000388 A KR1019820000388 A KR 1019820000388A KR 820000388 A KR820000388 A KR 820000388A KR 830008992 A KR830008992 A KR 830008992A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- compound
- formula
- chloromethyl
- chloroacetanilide
- Prior art date
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- 125000004970 halomethyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- -1 CF 3 group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000011968 lewis acid catalyst Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- RSFRCSYKTBSKPD-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,4-dimethylpent-2-en-3-yl)acetamide Chemical compound CC(C)C(=C(C)C)N(CCl)C(=O)CCl RSFRCSYKTBSKPD-UHFFFAOYSA-N 0.000 claims 1
- STVRVHDMZHCKDW-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,5-dimethylcyclopenten-1-yl)acetamide Chemical compound CC1CCC(C)=C1N(CCl)C(=O)CCl STVRVHDMZHCKDW-UHFFFAOYSA-N 0.000 claims 1
- FVNMFOXLAIDRMW-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-dimethylcyclohexen-1-yl)acetamide Chemical compound CC1CCCC(C)=C1N(CCl)C(=O)CCl FVNMFOXLAIDRMW-UHFFFAOYSA-N 0.000 claims 1
- GEBJACYJJFWANT-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2-ethyl-6-methylphenyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(CCl)C(=O)CCl GEBJACYJJFWANT-UHFFFAOYSA-N 0.000 claims 1
- CMCMKWMDDDLVSL-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2-methoxy-6-methylphenyl)acetamide Chemical compound COC1=CC=CC(C)=C1N(CCl)C(=O)CCl CMCMKWMDDDLVSL-UHFFFAOYSA-N 0.000 claims 1
- XRCVCJRSBHHWEN-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2-methyl-6-prop-2-enoxyphenyl)acetamide Chemical compound CC1=CC=CC(OCC=C)=C1N(CCl)C(=O)CCl XRCVCJRSBHHWEN-UHFFFAOYSA-N 0.000 claims 1
- HDBPBYZKQSZTCK-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(3-methylbut-2-en-2-yl)acetamide Chemical compound CC(C)=C(C)N(CCl)C(=O)CCl HDBPBYZKQSZTCK-UHFFFAOYSA-N 0.000 claims 1
- PLWNALCDLSVBIE-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-[2-ethyl-6-(2-methylpropoxy)phenyl]acetamide Chemical compound CCC1=CC=CC(OCC(C)C)=C1N(CCl)C(=O)CCl PLWNALCDLSVBIE-UHFFFAOYSA-N 0.000 claims 1
- UTPRVZATQNGTNH-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-[2-methyl-6-(2-methylpropoxy)phenyl]acetamide Chemical compound CC(C)COC1=CC=CC(C)=C1N(CCl)C(=O)CCl UTPRVZATQNGTNH-UHFFFAOYSA-N 0.000 claims 1
- JHOCCHYHYDIUEA-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=CC(C(F)(F)F)=C1N(CCl)C(=O)CCl JHOCCHYHYDIUEA-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CHEKZABCYJJZTL-UHFFFAOYSA-N n-(2-butoxy-6-ethylphenyl)-2-chloro-n-(chloromethyl)acetamide Chemical compound CCCCOC1=CC=CC(CC)=C1N(CCl)C(=O)CCl CHEKZABCYJJZTL-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (28)
- 루이스산 촉매하에서 염화치오닐 또는 브롬화치오닐과 구조식 II의 화합물의 반응을 포함하는 구조식 I의 화합물을 제조하는 방법.상기 구조식에서 X는 수소, 할로겐, C1-6알킬이나 할로알킬기, C3-7씨클로알킬기, 페닐이나 벤질기 또는 할로겐이나 니트로기, CF3기, C1-6알킬이나 알콕시기, 페닐이나 벤질기가 치환된 기들중의 어느 하나이다. R은 C1-20알킬기, 탄소수 10이상인 지방족 1-알켄-1-일기나 탄소수 7이상인 씨클로알킬이나 1-씨클로알켄-1-일기, 페닐기나 씨클로알킬기, 1-씨클로알켄-1-일기나 하나 또는 그 이상이 C1-6알킬, 알콕시, 알콕시알킬, C2-4알케닐, C3-4알케닐옥시, 니트로기나 트리플루오로메틸기나 할로겐기로 치환된 페닐기이다. R1은 탄소수 10이상을 갖는 하이드로 카빌기나 할로겐, C1-8알콕시, R2는 염소 또는 브롬원자이다.
- 1항에 있어서 반응은 0-100℃의 온도범위에서 행한다는 것.
- 2항에 있어서 온도는 환류(reflux)온도라는 것.
- 3항에 있어서 루이스산 촉매는 불화붕소에테르염이라는 것.
- 5항에 있어서 X는 염소원자라는 것.
- 5항에 있어서 R은 탄소수 10이상인 아씨클릭 1-알켄-1-일기라는 것.
- 6항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-N-[2-메틸-1-(1-메틸에틸)-1-프로페닐]-2-클로로아세트아미드라는 것.
- 6항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-N-(1,2-디메틸-1-프로펜일)-2-클로로아세트아미드라는 것.
- 5항에 있어서 R은 C5-71-씨클로알켄-1-일기나 하나 또는 그 이상이 C1-6알킬기로 임의 치환된 것이라는 것.
- 9항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-N-(2,6-디메틸-1-씨클로헥센-1-일)-2-클로로아세트아미드라는 것.
- 5항에 있어서 R이 페닐기나 C1-6알킬기, 알콕시기, 알콕시알킬기나 C2-4알케닐기, C3-4알케닐옥시기나 트리플루오로메틸기나 할로겐기로 하나 또는 그 이상이 임의 치환된 것이라는 것.
- 11항에 있어서 R은 양쪽 0-위치에 C1-6알킬기로 치환된 페닐기라는 것.
- 12항에 있어서 구조식 I의 화합물이 N-(클로로메틸)-2',6-디에틸-2-클로로아세트아닐리드라는 것.
- 12항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-메틸-6'-에틸-2-클로로아세트아닐리드라는 것.
- 11항에 있어서 R은 한쪽 0-위치는 C1-6알킬기로 치환되고 다른쪽 0-위치는 트리플루오로메틸기로 치환된 페닐기라는 것.
- 15항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-(트리플루메틸메틸)-6'-메틸-2-클로로아세트아닐리드라는 것.
- 15항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-(트리플루오로메틸)-6'-메틸-2-클로로아세트아닐리드라는 것.
- 11항에 있어서 R은 양쪽 0-위치는 C1-6알킬기로 치환되고 다른쪽 0-위치는 C1-6알콕시나 C3-4알타닐옥시기로 치환된 페닐기라는 것.
- 18항에 있어서 기술한 알킬기가 메톡시나 C3-4알콕시기라는 것.
- 18항에 있어서 기술한 알콕시기가 메톡시나 C3-4알콕시기라는 것.
- 20항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-메톡시-6'-메틸-2-클로로아세트아닐리드라는 것.
- 20항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-이소푸로폭시-6'-메틸-2-클로로아세트아닐리드라는 것.
- 20항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-이소부톡시-6'-메틸-2-클로로아세트아닐리드라는 것.
- 20항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-이소부톡시-6'-에틸-2-클로로아세트아닐리드라는 것.
- 20항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-n-부톡시-6'-에틸-2-클로로아세트아닐리드라는 것.
- 19항에 있어서 기재된 0-위치가 C3-4알케닐옥시기로 공유된 것이라는 것.
- 26항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-2'-(1-프로펜-3-일옥시)-6'-메틸-2-클로로아세트아닐리드라는 것.
- 9항에 있어서 구조식 I의 화합물은 N-(클로로메틸)-N-(2,5-디메틸-1-씨클로펜텐-1-일)-2-클로로아세트아미드라는 것.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/230,576 US4322553A (en) | 1981-02-02 | 1981-02-02 | Process for producing N-(halomethyl)acylamides |
| US230576 | 1981-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830008992A true KR830008992A (ko) | 1983-12-16 |
| KR860000261B1 KR860000261B1 (ko) | 1986-03-22 |
Family
ID=22865736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200388A KR860000261B1 (ko) | 1981-02-02 | 1982-01-29 | N-(할로메틸)아씰아미드의 제조방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4322553A (ko) |
| EP (1) | EP0057588B1 (ko) |
| JP (1) | JPS57144249A (ko) |
| KR (1) | KR860000261B1 (ko) |
| AR (1) | AR229356A1 (ko) |
| AT (1) | ATE6774T1 (ko) |
| AU (1) | AU540246B2 (ko) |
| BR (1) | BR8200503A (ko) |
| CA (1) | CA1181424A (ko) |
| CS (1) | CS226045B2 (ko) |
| DD (1) | DD201585A5 (ko) |
| DE (1) | DE3260070D1 (ko) |
| ES (1) | ES8303296A1 (ko) |
| GB (1) | GB2092148B (ko) |
| HU (1) | HU187563B (ko) |
| IL (1) | IL64897A (ko) |
| MY (1) | MY8600281A (ko) |
| NO (1) | NO820281L (ko) |
| NZ (1) | NZ199607A (ko) |
| PL (1) | PL131478B1 (ko) |
| RO (1) | RO85558A (ko) |
| YU (1) | YU12482A (ko) |
| ZA (1) | ZA82606B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3123731A1 (de) * | 1981-06-15 | 1982-12-30 | Basf Ag, 6700 Ludwigshafen | Chloressigsaeurecyclohexylamide, ihre herstellung, ihre verwendung zur herbizidbekaempfung und mittel dafuer |
| US4798618A (en) * | 1981-12-10 | 1989-01-17 | Agro-Kanesho Co., Ltd. | Novel chloroacetanilide derivatives and herbicides containing the same for use in paddy field |
| DE3206660A1 (de) * | 1982-02-25 | 1983-09-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o-acylamidomethylbenzyl-halogeniden |
| US4935053A (en) * | 1989-06-12 | 1990-06-19 | Air Products And Chemicals, Inc. | Unsaturated haloacetanilides |
| US4994105A (en) * | 1989-06-12 | 1991-02-19 | Air Products And Chemicals, Inc. | N,N'-bis(alkoxyalkyl)-N,N'-(2-haloacetyl)phenylenediamines |
| JOP20180077A1 (ar) | 2007-06-19 | 2019-01-30 | Kythera Biopharmaceuticals Inc | تركيبات وطرق لحمض صفراوي تخليقي |
| US8242294B2 (en) * | 2007-06-19 | 2012-08-14 | Kythera Biopharmaceuticals, Inc. | Synthetic bile acid compositions and methods |
| US20080318870A1 (en) * | 2007-06-19 | 2008-12-25 | Kythera Biopharmaceuticals, Inc. | Synthetic bile acid compositions and methods |
| DE102008057718B4 (de) | 2008-11-17 | 2020-02-06 | Skw Stickstoffwerke Piesteritz Gmbh | Verfahren zur regioselektiven Herstellung von N-(1H-Pyrazolylmethyl)-amiden |
| BR112013003216A2 (pt) | 2010-08-12 | 2016-05-17 | Kythera Biopharmaceuticals Inc | composições sintéticas de ácido biliar e métodos |
| CN111302968B (zh) * | 2020-03-20 | 2021-06-08 | 中国科学院上海有机化学研究所 | 一种酰胺氮三氟甲基化合物的合成方法 |
| CN117964512B (zh) * | 2024-04-01 | 2024-06-04 | 山东惟普控股有限公司 | 一种n,n-二甲基-3-甲氧基丙酰胺的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259540A (en) * | 1961-02-13 | 1966-07-05 | Murphy Chemical Ltd | Stabilized insecticidal composition containing an o, o-dimethyl s-(n-alkoxymethyl) carbamoylmethyl phosphorothiolothionate |
| JPS5346949A (en) * | 1976-10-07 | 1978-04-27 | Kao Corp | 1-haldgenotricyclo(4,3,1,12,5)undecanes and their preparation |
| DE2828293A1 (de) * | 1978-06-28 | 1980-01-10 | Bayer Ag | N-dichloracetyl-1,2,3,4-tetrahydro- chinaldin, verfahren zu dessen herstellung und dessen verwendung zur verhuetung von herbizidschaeden an kulturpflanzen |
-
1981
- 1981-02-02 US US06/230,576 patent/US4322553A/en not_active Expired - Fee Related
-
1982
- 1982-01-19 YU YU00124/82A patent/YU12482A/xx unknown
- 1982-01-29 CA CA000395223A patent/CA1181424A/en not_active Expired
- 1982-01-29 AR AR288284A patent/AR229356A1/es active
- 1982-01-29 GB GB8202574A patent/GB2092148B/en not_active Expired
- 1982-01-29 EP EP82300470A patent/EP0057588B1/en not_active Expired
- 1982-01-29 ES ES509171A patent/ES8303296A1/es not_active Expired
- 1982-01-29 RO RO82108480A patent/RO85558A/ro unknown
- 1982-01-29 ZA ZA82606A patent/ZA82606B/xx unknown
- 1982-01-29 JP JP57011930A patent/JPS57144249A/ja active Pending
- 1982-01-29 CS CS82635A patent/CS226045B2/cs unknown
- 1982-01-29 DD DD82237072A patent/DD201585A5/de unknown
- 1982-01-29 KR KR8200388A patent/KR860000261B1/ko active
- 1982-01-29 NO NO820281A patent/NO820281L/no unknown
- 1982-01-29 HU HU82277A patent/HU187563B/hu unknown
- 1982-01-29 PL PL1982234873A patent/PL131478B1/pl unknown
- 1982-01-29 BR BR8200503A patent/BR8200503A/pt unknown
- 1982-01-29 AT AT82300470T patent/ATE6774T1/de active
- 1982-01-29 IL IL64897A patent/IL64897A/xx unknown
- 1982-01-29 AU AU79977/82A patent/AU540246B2/en not_active Ceased
- 1982-01-29 NZ NZ199607A patent/NZ199607A/en unknown
- 1982-01-29 DE DE8282300470T patent/DE3260070D1/de not_active Expired
-
1986
- 1986-12-30 MY MY281/86A patent/MY8600281A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES509171A0 (es) | 1983-02-01 |
| EP0057588A2 (en) | 1982-08-11 |
| DD201585A5 (de) | 1983-07-27 |
| MY8600281A (en) | 1986-12-31 |
| EP0057588A3 (en) | 1982-08-25 |
| ES8303296A1 (es) | 1983-02-01 |
| JPS57144249A (en) | 1982-09-06 |
| IL64897A0 (en) | 1982-03-31 |
| PL234873A1 (ko) | 1982-08-16 |
| NZ199607A (en) | 1985-07-12 |
| ATE6774T1 (de) | 1984-04-15 |
| HU187563B (en) | 1986-01-28 |
| AR229356A1 (es) | 1983-07-29 |
| DE3260070D1 (en) | 1984-04-26 |
| AU7997782A (en) | 1982-08-12 |
| NO820281L (no) | 1982-08-03 |
| GB2092148A (en) | 1982-08-11 |
| CA1181424A (en) | 1985-01-22 |
| CS226045B2 (en) | 1984-03-19 |
| YU12482A (en) | 1985-03-20 |
| BR8200503A (pt) | 1982-12-07 |
| PL131478B1 (en) | 1984-11-30 |
| KR860000261B1 (ko) | 1986-03-22 |
| GB2092148B (en) | 1985-06-26 |
| RO85558A (ro) | 1984-11-25 |
| EP0057588B1 (en) | 1984-03-21 |
| IL64897A (en) | 1985-08-30 |
| US4322553A (en) | 1982-03-30 |
| ZA82606B (en) | 1983-01-26 |
| AU540246B2 (en) | 1984-11-08 |
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