CH624097A5 - - Google Patents
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- Publication number
- CH624097A5 CH624097A5 CH1594575A CH1594575A CH624097A5 CH 624097 A5 CH624097 A5 CH 624097A5 CH 1594575 A CH1594575 A CH 1594575A CH 1594575 A CH1594575 A CH 1594575A CH 624097 A5 CH624097 A5 CH 624097A5
- Authority
- CH
- Switzerland
- Prior art keywords
- coome
- pyrolysis
- cook
- formula
- nrr
- Prior art date
Links
- 238000000034 method Methods 0.000 claims 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 5
- 238000000197 pyrolysis Methods 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/34—Ethylene-urea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
624097
2
Claims (4)
1
N-R
C
h
0
dove n = 2, 3, 4 e dove R e R' sono idrogeno, radicali al-chilici o arilici, cicloalchilici, arilalchilici o alchilarilici, sostituiti e non, caratterizzato dalla pirolisi dei corrispondenti carbammati di formula
N
R
RR'N-COOMe oppure (CH2)n
N
R
dove Me è un metallo alcalino, a temperature comprese fra 150 e400°C.
2. Procedimento secondo la rivendicazione 1, eseguito sotto pressione ridotta.
3. Procedimento secondo la rivendicazione 2, nel quale il C,;Hr,NH-COOLi è sottoposto alla pirolisi a ca. 3Q0°C e 20 mm Hg ed è ottenuta la difenilurea.
4. Procedimento secondo la rivendicazione 2, nel quale il
CH3
H.,C—N—COOK
I
H..C—N—COOK
I
ch3
è sottoposto alla pirolisi a ca. 350°C e 20 mm Hg ed è ottenuta la N,N'-dimetiletilenurea.
La presente invenzione concerne un procedimento per la preparazione di uree di formula:
c
II
0
io dove n = 2, 3, 4 e dove R ed R' sono idrogeno, radicali al-chilici o arilici, cicloalchilici, arilalchilici o alchilarilici, sostituiti o non, caratterizzato dalla pirolisi dei corrispondenti carbammati di formula:
15
N
20
RR'N-COOMe oppure (CHg)n
COOMe
N
.COOMe 25
COOMe COOMe
R
dove Me è un metallo alcalino o alcalino-terroso. Tali carbammati possono essere preparati per esempio, secondo un procedimento descritto nella domanda di brevetto svizzera n. 15944/75 depositata il giorno 8 dicembre 1975.
30 La pirolisi avviene secondo lo schema di reazione seguente:
A
2 RR'N-COOMe RR'N-CO-NRR' + Me2C03
35
a temperature comprese tra 150 e 400°C, a pressione ambiente o, preferibilmente, sotto vuoto; in tali condizioni l'urea distilla o sublima.
40 Esempio 1
20 g di C.jHg-NH-COOLi vengono messi in una provetta codata, inserita in un fornetto elettrico ed alla quale è fatto un vuoto di 20 mmHg.
Si scalda il forno a 300°C e sulle pareti della provetta
45 sublimano g 14 di difenilurea; il residuo è costituito da 6 g di Li2CO;ì.
20 g di
50
55
Esempio 2 CH3
ch2—n—cook ch2—n—cook
I
ch3
vengono trattati come sopra a 350°C; distillato 9 g di N,N'--dimetiletilenurea; il residuo (11 g) è costituito da K2C03.
v
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30341/74A IT1026907B (it) | 1974-12-10 | 1974-12-10 | Procedimento per la sintesi di uree |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624097A5 true CH624097A5 (it) | 1981-07-15 |
Family
ID=11229569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1594575A CH624097A5 (it) | 1974-12-10 | 1975-12-08 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4063021A (it) |
| JP (1) | JPS594423B2 (it) |
| AT (1) | AT349487B (it) |
| BE (1) | BE836387A (it) |
| CA (1) | CA1058174A (it) |
| CH (1) | CH624097A5 (it) |
| DE (1) | DE2555582A1 (it) |
| DK (1) | DK557075A (it) |
| ES (1) | ES443591A1 (it) |
| FR (1) | FR2294169A1 (it) |
| GB (1) | GB1499180A (it) |
| IE (1) | IE42456B1 (it) |
| IT (1) | IT1026907B (it) |
| LU (1) | LU73953A1 (it) |
| NL (1) | NL172951C (it) |
| NO (1) | NO754162L (it) |
| SE (1) | SE431203B (it) |
| SU (1) | SU900804A3 (it) |
| ZA (1) | ZA757617B (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE29820895U1 (de) | 1998-11-23 | 1999-02-18 | ECS Eich Maschinenbau GmbH, 35745 Herborn | Mobiles Wasserreinigungsgerät |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57139069A (en) * | 1981-02-20 | 1982-08-27 | Nippon Tokushu Noyaku Seizo Kk | Substituted tetrahydropyrimidinone derivative, its preparation and herbicide |
| US4405794A (en) * | 1981-12-18 | 1983-09-20 | The Dow Chemical Company | Preparation of 2-oxazolidinone and ethyleneurea |
| JPS58140078A (ja) * | 1982-02-16 | 1983-08-19 | Nippon Tokushu Noyaku Seizo Kk | メチル置換テトラヒドロ−２−ピリミジノン誘導体、その製法、その中間体及び該中間体の製法、並びに除草剤 |
| JPH0333420U (it) * | 1989-08-10 | 1991-04-02 | ||
| DE19743760A1 (de) * | 1997-10-02 | 1999-04-08 | Basf Ag | Verfahren zur Herstellung von cyclischen Harnstoffderivaten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2276696A (en) * | 1939-10-06 | 1942-03-17 | Sharples Chemicals Inc | Manufacture of homologues of urea |
| US3053891A (en) * | 1959-05-05 | 1962-09-11 | Chemical Construction Corp | Process for production of urea |
| US3923833A (en) * | 1968-05-01 | 1975-12-02 | Hoffmann La Roche | N-{8 (1-cyano-2-phenyl)ethyl{9 carbamates |
-
1974
- 1974-12-10 IT IT30341/74A patent/IT1026907B/it active
-
1975
- 1975-12-04 ZA ZA757617A patent/ZA757617B/xx unknown
- 1975-12-04 CA CA241,089A patent/CA1058174A/en not_active Expired
- 1975-12-08 LU LU73953A patent/LU73953A1/xx unknown
- 1975-12-08 CH CH1594575A patent/CH624097A5/it not_active IP Right Cessation
- 1975-12-08 FR FR7537465A patent/FR2294169A1/fr active Granted
- 1975-12-08 BE BE162536A patent/BE836387A/xx not_active IP Right Cessation
- 1975-12-08 GB GB50307/75A patent/GB1499180A/en not_active Expired
- 1975-12-09 NO NO754162A patent/NO754162L/no unknown
- 1975-12-09 ES ES443591A patent/ES443591A1/es not_active Expired
- 1975-12-09 DK DK557075A patent/DK557075A/da not_active Application Discontinuation
- 1975-12-09 SE SE7513879A patent/SE431203B/xx unknown
- 1975-12-09 NL NLAANVRAGE7514362,A patent/NL172951C/xx not_active IP Right Cessation
- 1975-12-09 AT AT933175A patent/AT349487B/de not_active IP Right Cessation
- 1975-12-10 JP JP50146470A patent/JPS594423B2/ja not_active Expired
- 1975-12-10 DE DE19752555582 patent/DE2555582A1/de active Pending
- 1975-12-10 SU SU752197703A patent/SU900804A3/ru active
- 1975-12-10 US US05/639,441 patent/US4063021A/en not_active Expired - Lifetime
- 1975-12-10 IE IE2693/75A patent/IE42456B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE29820895U1 (de) | 1998-11-23 | 1999-02-18 | ECS Eich Maschinenbau GmbH, 35745 Herborn | Mobiles Wasserreinigungsgerät |
Also Published As
| Publication number | Publication date |
|---|---|
| LU73953A1 (it) | 1976-07-01 |
| SE7513879L (sv) | 1976-06-11 |
| NL7514362A (nl) | 1976-06-14 |
| BE836387A (fr) | 1976-06-08 |
| DK557075A (da) | 1976-06-11 |
| CA1058174A (en) | 1979-07-10 |
| NO754162L (it) | 1976-06-11 |
| IT1026907B (it) | 1978-10-20 |
| FR2294169A1 (fr) | 1976-07-09 |
| SU900804A3 (ru) | 1982-01-23 |
| FR2294169B1 (it) | 1982-05-28 |
| IE42456B1 (en) | 1980-08-13 |
| NL172951C (nl) | 1983-11-16 |
| ES443591A1 (es) | 1977-05-01 |
| US4063021A (en) | 1977-12-13 |
| NL172951B (nl) | 1983-06-16 |
| JPS5182225A (it) | 1976-07-19 |
| ATA933175A (de) | 1978-09-15 |
| DE2555582A1 (de) | 1976-06-16 |
| IE42456L (en) | 1976-06-10 |
| SE431203B (sv) | 1984-01-23 |
| JPS594423B2 (ja) | 1984-01-30 |
| GB1499180A (en) | 1978-01-25 |
| ZA757617B (en) | 1976-11-24 |
| AT349487B (de) | 1979-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |