GB811692A - Improvements in or relating to chlorobenzimidazolone compounds - Google Patents
Improvements in or relating to chlorobenzimidazolone compoundsInfo
- Publication number
- GB811692A GB811692A GB1192857A GB1192857A GB811692A GB 811692 A GB811692 A GB 811692A GB 1192857 A GB1192857 A GB 1192857A GB 1192857 A GB1192857 A GB 1192857A GB 811692 A GB811692 A GB 811692A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- dichloro
- reacting
- ethyl
- nitro
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0811692/IV (b)/1> wherein R is an ethyl or an allyl group and X and Y are hydrogen or chlorine atoms in the combination 5-chloro, 6-chloro- or 5,6-dichloro, and the manufacture thereof by (a) reacting at temperatures above 75 DEG C. a phenylenediamine compound of the formula: <FORM:0811692/IV (b)/2> with a carbonic acid derivative such as a dialkyl carbonate, an alkyl, aralkyl or aryl chloroformate, a urea, phosgene, an alkyl or aryl isocyanate or urethane or a dialkyliminocarbonate; (b) cyclizing a N-acyl phenylenediamine of the general formula: <FORM:0811692/IV (b)/3> wherein Z is an alkoxy, amino or substituted amino group, at elevated temperature in the presence of a basic condensation catalyst; and (c) subjecting a 1-isopropenyl-chlorobenzimidazolone of the general formula: <FORM:0811692/IV (b)/4> to acid hydrolysis in the presence of a solvent. Examples describe the preparation by process (a) of 6-chloro-1-ethylbenzimidazolone by reacting 5 - chloro - N1 - ethylphenylene - 1,2-diamine and ethyl carbonate in the presence of sodium methoxide, of 5 : 6-dichloro-1-ethylbenzimidazolone and of 1-allyl-6-chloro-, 5-chloro-, and -5,6-dichloro-benzimidazoles by reacting the corresponding diamines with urea in boiling 2-butoxyethanol; by process (b) of 5- and 6-chloro-1-ethylbenzimidazoles from 4- and 5 - chloro - N1 - carbethoxy - N1 - ethylphenylenediamines respectively, using sodium ethoxide as the basic condensation catalyst; and by process (c) of 1-allyl-5,6-dichlorobenzimidazolone by first reacting 4,5-dichlorophenylene-1,2-diamine with ethyl acetoacetate and then with sodium and 2-ethoxyethanol to give a reaction mixture containing 5,6-dichloro-1 - isopropenylbenzimidazolone, treating this with allyl bromide to give 3-allyl-5,6-dichloroisopropenylbenzimidazolone, and hydrolysing with concentrated hydrochloric acid. An example describes the preparation of 5,6-dichloro-1-ethylbenzimidazolone by reacting 4,5 - dichloro - N - ethyl - 2 - nitroaniline with butyl chloroformate, hydrogenating the product in the presence of a platinum oxide catalyst and then with sodium and 2-ethoxyethanol. 4 : 5 - Dichloro - and 5 - chloro - N1 - ethylphenylenediamines, 5 - chloro -, 4 - chloro - and 4 : 5 - dichloro - N1 - allylphenylenediamines are prepared by reducing 4 : 5-dichloro- and 5-chloro - 2 - nitro - N - ethylaniline, 5 - chloro -, 4 - chloro - and 4 : 5 - dichloro - 2 - nitro - N - allylanilines, respectively with iron in an aqueous acidic medium. 4 : 5 - Dichloro - and 5 - chloro - 2 - nitro - N - ethylanilines, and 4 : 5 - dichloro - 2 - nitro - N - allylaniline are prepared from 2 : 4 : 5-trichloro- and 2 : 4-dichloronitrobenzenes and ethyl- and allylamines. 5 - Chloro - N1 - carbethoxy - N1 - ethylphenylenediamine is prepared by reacting 5-chloro-N-ethyl-2-nitroaniline with ethylchloroformate and hydrogenating the resultant 5-chloro-2-nitro-N-carbethoxy-N-ethylaniline.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1192857A GB811692A (en) | 1957-04-11 | 1957-04-11 | Improvements in or relating to chlorobenzimidazolone compounds |
DEP20477A DE1115740B (en) | 1957-04-11 | 1958-04-09 | Process for the preparation of chlorobenzimidazolones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1192857A GB811692A (en) | 1957-04-11 | 1957-04-11 | Improvements in or relating to chlorobenzimidazolone compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB811692A true GB811692A (en) | 1959-04-08 |
Family
ID=9995219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1192857A Expired GB811692A (en) | 1957-04-11 | 1957-04-11 | Improvements in or relating to chlorobenzimidazolone compounds |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1115740B (en) |
GB (1) | GB811692A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3167586A (en) * | 1961-11-06 | 1965-01-26 | Monsanto Co | Preparation of cis-1, 2-diaminocyclo-hexane |
US3413350A (en) * | 1965-03-09 | 1968-11-26 | Mobay Chemical Corp | Purification of aromatic diamines |
US4113952A (en) * | 1977-07-22 | 1978-09-12 | The Sherwin-Williams Company | Process for preparing 2-benzimidazolones |
US4138568A (en) * | 1976-06-11 | 1979-02-06 | Ciba-Geigy Corporation | Process for the manufacture of benzimidazolones-(2) |
CN116514723A (en) * | 2023-03-22 | 2023-08-01 | 上海麦克林生化科技股份有限公司 | Synthesis method of 5, 6-2-chloro-1-ethyl-1H-benzimidazole-2-one (DCEBIO) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2855226A1 (en) * | 1978-12-21 | 1980-07-10 | Hoechst Ag | METHOD FOR PRODUCING BENZIMIDAZOLONE (2) |
-
1957
- 1957-04-11 GB GB1192857A patent/GB811692A/en not_active Expired
-
1958
- 1958-04-09 DE DEP20477A patent/DE1115740B/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3167586A (en) * | 1961-11-06 | 1965-01-26 | Monsanto Co | Preparation of cis-1, 2-diaminocyclo-hexane |
US3413350A (en) * | 1965-03-09 | 1968-11-26 | Mobay Chemical Corp | Purification of aromatic diamines |
US3414619A (en) * | 1965-03-09 | 1968-12-03 | Mobay Chemical Corp | Purification of aromatic diamines |
US4138568A (en) * | 1976-06-11 | 1979-02-06 | Ciba-Geigy Corporation | Process for the manufacture of benzimidazolones-(2) |
US4113952A (en) * | 1977-07-22 | 1978-09-12 | The Sherwin-Williams Company | Process for preparing 2-benzimidazolones |
CN116514723A (en) * | 2023-03-22 | 2023-08-01 | 上海麦克林生化科技股份有限公司 | Synthesis method of 5, 6-2-chloro-1-ethyl-1H-benzimidazole-2-one (DCEBIO) |
Also Published As
Publication number | Publication date |
---|---|
DE1115740B (en) | 1961-10-26 |
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