GB1327294A - Process for the preparation of alpha-anilinocarboxylic esters or nitriles - Google Patents
Process for the preparation of alpha-anilinocarboxylic esters or nitrilesInfo
- Publication number
- GB1327294A GB1327294A GB1327294DA GB1327294A GB 1327294 A GB1327294 A GB 1327294A GB 1327294D A GB1327294D A GB 1327294DA GB 1327294 A GB1327294 A GB 1327294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alpha
- general formula
- group
- nitrile
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002825 nitriles Chemical class 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- SKBGHSYTMQEDCY-UHFFFAOYSA-N 2-(4-chloro-3-fluoroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(Cl)C(F)=C1 SKBGHSYTMQEDCY-UHFFFAOYSA-N 0.000 abstract 1
- KMWRISRTGYELKS-UHFFFAOYSA-N 2-(4-fluoroanilino)propanenitrile Chemical compound N#CC(C)NC1=CC=C(F)C=C1 KMWRISRTGYELKS-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- -1 aniline compound Chemical class 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000075 primary alcohol group Chemical group 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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
1327294 Preparation of alpha-anilino carboxylic esters and nitriles SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 30 April 1971 12410/71 Heading C2C Alpha-anilino carboxylic esters of the general formula in which R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> each individually represent a halogen atom or an alkyl, haloalkyl or alkoxy group, while R<SP>1</SP> and/or R<SP>2</SP> may also be hydrogen atoms, and R<SP>2</SP> may also be a group -NH-CH(R<SP>4</SP>)-X or a group -(A) n - C @ H 2 (R<SP>1</SP>,R<SP>3</SP>)-NH-CH(R<SP>4</SP>)-X, in which A=CH 2 ), S or NH and n=zero or 1; R<SP>4</SP> is a hydrogen atom or an alkyl group and X is a carboxylic ester group are prepared by reacting a nitrile of the general formula with a primary or secondary alcohol in the presence of hydrogen chloride or bromide, first (a) at a temperature ranging from - 20‹ C. to + 70‹ C. for a time not exceeding that necessary for the conversion of at least 70% of the nitrile, and subsequently (b) at a temperature ranging from 55‹ to 150‹ C.-with the proviso that at least during the time interval (a) the amount of HC1 or HBr present should be greater than 3À5 equivalents, based on the nitrile, while the concentration of the said hydrohalide in the reaction medium should be at least 4 mole per litre. The ester may be converted to the alpha- (N-acylanilino) carboxylic ester by reacting with an acylating agent, e.g. benzoyl chloride. Alpha-anilino carbonitriles of the general Formula II above may be prepared by reacting in an alcoholic medium an aniline compound of the general formula with either (a) hydrogen cyanide and an aldehyde R<SP>4</SP>-CHO or (b) a cyanohydrin R<SP>4</SP>-CH(OH)-CN, in the additional presence in the case being of a strong base. Compounds claimed per se are alpha-(4-fluoroanilino) propiononitrile, alpha - (4 - chloro - 3 - fluoroanilino) propiononitrile.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1241071 | 1971-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1327294A true GB1327294A (en) | 1973-08-22 |
Family
ID=10004092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1327294D Expired GB1327294A (en) | 1971-04-30 | 1971-04-30 | Process for the preparation of alpha-anilinocarboxylic esters or nitriles |
Country Status (18)
| Country | Link |
|---|---|
| JP (2) | JPS5749537B1 (en) |
| BE (1) | BE782595A (en) |
| CA (1) | CA982141A (en) |
| CH (1) | CH589049A5 (en) |
| CS (1) | CS195255B2 (en) |
| DD (1) | DD101889A5 (en) |
| DE (1) | DE2221109C2 (en) |
| DK (1) | DK153472C (en) |
| ES (1) | ES402224A1 (en) |
| FR (1) | FR2139847B1 (en) |
| GB (1) | GB1327294A (en) |
| HU (1) | HU164835B (en) |
| IT (1) | IT953845B (en) |
| NL (1) | NL175173C (en) |
| PL (1) | PL83652B1 (en) |
| RO (1) | RO62750A (en) |
| SU (1) | SU461492A3 (en) |
| YU (1) | YU39269B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1547758A (en) * | 1975-07-29 | 1979-06-27 | Shell Int Research | Herbicidal composition |
| CH624925A5 (en) * | 1976-05-08 | 1981-08-31 | Basf Ag | Process for the preparation of glycinenitriles |
| US4318920A (en) * | 1979-02-08 | 1982-03-09 | Abbott Laboratories | Ovicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE151538C (en) * | ||||
| NL136594C (en) * | 1965-10-22 | |||
| US3463805A (en) * | 1967-05-08 | 1969-08-26 | Grace W R & Co | Production of aminonitriles under adiabatic conditions |
| GB1307978A (en) * | 1969-02-28 | 1973-02-21 | Wellcome Found | Amidines processes for their preparation and pharmaceutical compo sitions incorporating the same |
-
1971
- 1971-04-30 GB GB1327294D patent/GB1327294A/en not_active Expired
-
1972
- 1972-04-25 BE BE782595A patent/BE782595A/en not_active IP Right Cessation
- 1972-04-27 DK DK212772A patent/DK153472C/en not_active IP Right Cessation
- 1972-04-27 NL NL7205688A patent/NL175173C/en not_active IP Right Cessation
- 1972-04-28 SU SU1778332A patent/SU461492A3/en active
- 1972-04-28 FR FR7215325A patent/FR2139847B1/fr not_active Expired
- 1972-04-28 IT IT2369672A patent/IT953845B/en active
- 1972-04-28 CH CH639572A patent/CH589049A5/xx not_active IP Right Cessation
- 1972-04-28 JP JP47042319A patent/JPS5749537B1/ja active Pending
- 1972-04-28 CS CS289572A patent/CS195255B2/en unknown
- 1972-04-28 ES ES402224A patent/ES402224A1/en not_active Expired
- 1972-04-28 PL PL15504972A patent/PL83652B1/pl unknown
- 1972-04-28 DD DD16264872A patent/DD101889A5/xx unknown
- 1972-04-28 DE DE19722221109 patent/DE2221109C2/en not_active Expired
- 1972-04-28 RO RO7073672A patent/RO62750A/en unknown
- 1972-04-28 CA CA140,875A patent/CA982141A/en not_active Expired
- 1972-04-28 HU HUSE001623 patent/HU164835B/hu not_active IP Right Cessation
- 1972-05-03 YU YU115772A patent/YU39269B/en unknown
-
1980
- 1980-07-30 JP JP10378180A patent/JPS5639057A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU461492A3 (en) | 1975-02-25 |
| NL175173C (en) | 1984-10-01 |
| DK153472B (en) | 1988-07-18 |
| JPS5736274B2 (en) | 1982-08-03 |
| RO62750A (en) | 1977-10-15 |
| IT953845B (en) | 1973-08-10 |
| CA982141A (en) | 1976-01-20 |
| PL83652B1 (en) | 1975-12-31 |
| FR2139847B1 (en) | 1973-12-07 |
| YU115772A (en) | 1982-05-31 |
| DK153472C (en) | 1988-11-21 |
| NL175173B (en) | 1984-05-01 |
| JPS5639057A (en) | 1981-04-14 |
| CH589049A5 (en) | 1977-06-30 |
| HU164835B (en) | 1974-04-11 |
| NL7205688A (en) | 1972-11-01 |
| JPS5749537B1 (en) | 1982-10-22 |
| CS195255B2 (en) | 1980-01-31 |
| YU39269B (en) | 1984-10-31 |
| DE2221109A1 (en) | 1972-11-16 |
| DD101889A5 (en) | 1973-11-20 |
| FR2139847A1 (en) | 1973-01-12 |
| DE2221109C2 (en) | 1983-10-06 |
| AU4168072A (en) | 1973-11-01 |
| ES402224A1 (en) | 1976-01-01 |
| BE782595A (en) | 1972-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |