GB1198633A - Phenyl-Sulphonated Benzimidazoles - Google Patents
Phenyl-Sulphonated BenzimidazolesInfo
- Publication number
- GB1198633A GB1198633A GB5353567A GB5353567A GB1198633A GB 1198633 A GB1198633 A GB 1198633A GB 5353567 A GB5353567 A GB 5353567A GB 5353567 A GB5353567 A GB 5353567A GB 1198633 A GB1198633 A GB 1198633A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- group
- reacting
- nitro
- phenyl
- 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
- 150000001556 benzimidazoles Chemical class 0.000 title abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- YNEBJKKWUZNVFY-UHFFFAOYSA-N 1,4-bis-(4-methylphenyl)sulfonyl-2-nitrobenzene Chemical compound C1(=CC=C(C=C1)S(=O)(=O)C1=C(C=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)C)[N+](=O)[O-])C YNEBJKKWUZNVFY-UHFFFAOYSA-N 0.000 abstract 1
- WSLKRDDYWLCINP-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfonyl-2-nitrobenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 WSLKRDDYWLCINP-UHFFFAOYSA-N 0.000 abstract 1
- HQGIKKNMQKODQS-UHFFFAOYSA-N 2-(benzenesulfonyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)(=O)C1=CC=CC=C1 HQGIKKNMQKODQS-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- PUVHOIFJGJIVRT-UHFFFAOYSA-N 2-[4-(4-methylphenyl)sulfonyl-2-nitroanilino]ethanol Chemical compound OCCNC1=C(C=C(C=C1)S(=O)(=O)C1=CC=C(C=C1)C)[N+](=O)[O-] PUVHOIFJGJIVRT-UHFFFAOYSA-N 0.000 abstract 1
- WOEVJEOAYZXSEB-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-N-ethyl-2-nitroaniline Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(NCC)C=C1)[N+](=O)[O-] WOEVJEOAYZXSEB-UHFFFAOYSA-N 0.000 abstract 1
- RUZCDLMYLTUSGB-UHFFFAOYSA-N 4-(benzenesulfonyl)-1-chloro-2-nitrobenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 RUZCDLMYLTUSGB-UHFFFAOYSA-N 0.000 abstract 1
- FSYMYVKFFGTZDZ-UHFFFAOYSA-N 4-(benzenesulfonyl)-N-ethyl-2-nitroaniline Chemical compound C(C)NC1=C(C=C(C=C1)S(=O)(=O)C1=CC=CC=C1)[N+](=O)[O-] FSYMYVKFFGTZDZ-UHFFFAOYSA-N 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,198,633. Phenylsulphonyl - benzimidazoles. ILFORD Ltd. 24 Nov., 1967 [28 Nov., 1966], No. 53535/67. Heading C2C. The invention comprises benzimidazoles of the general formula wherein R is hydrogen or an alkyl, hydroxy alkyl, aryl or aralkyl group, Q is phenyl or phenyl substituted with at least one halogen, alkyl or alkoxy substituent and X is hydrogen or lower alkyl C 1-4 , which are prepared by reacting a compound of the formula wherein T is either a group -QSO 2 or a halogen atom where Q is as defined above, with ammonia or an amine of the formula RNH 2 , where R is as defined above, to replace the group T by NHR, reducing the -NO 2 group to an -NH 2 group, and effecting ring closure with an organic acid of the formula XCOOH where X is as defined above, or with an acid chloride or anhydride thereof. N - Ethyl - 2 - nitro - 4 - phenylsulphonylaniline is prepared by reacting 4-chloro-3- nitrophenyl phenyl sulphone with ethylamine. N - Ethyl - 2 - nitro - 4 - p - chlorophenylsulphonylaniline is prepared by reacting 4- chloro - 3 - nitrophenyl 4 - chlorophenylsulphone with ethylamine. 4 - (2,4 - Dichlorophenyl) - sulphonyl - 2 - nitrodiphenylamine is prepared by reacting 4 - chloro - 3 - nitro 2,4 - dichlorophenyl sulphone with aniline. N - (2 - Hydroxyethyl) - 2 - nitro - 4 - p - tolylsulphonylaniline is prepared by reacting ethylamine with 1,4-di-p-tolylsulphonyl-2-nitrobenzene. The corresponding diamino compounds are prepared by reducing the nitro group in the 2-position by iron and hydrochloric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5353567A GB1198633A (en) | 1967-11-24 | 1967-11-24 | Phenyl-Sulphonated Benzimidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5353567A GB1198633A (en) | 1967-11-24 | 1967-11-24 | Phenyl-Sulphonated Benzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1198633A true GB1198633A (en) | 1970-07-15 |
Family
ID=10468148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5353567A Expired GB1198633A (en) | 1967-11-24 | 1967-11-24 | Phenyl-Sulphonated Benzimidazoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1198633A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7598393B2 (en) | 2004-11-02 | 2009-10-06 | Pfizer Inc. | Sulfonyl benzimidazole derivatives |
-
1967
- 1967-11-24 GB GB5353567A patent/GB1198633A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7598393B2 (en) | 2004-11-02 | 2009-10-06 | Pfizer Inc. | Sulfonyl benzimidazole derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |