GB703272A - Manufacture of new derivatives of benzimidazole - Google Patents
Manufacture of new derivatives of benzimidazoleInfo
- Publication number
- GB703272A GB703272A GB516151A GB516151A GB703272A GB 703272 A GB703272 A GB 703272A GB 516151 A GB516151 A GB 516151A GB 516151 A GB516151 A GB 516151A GB 703272 A GB703272 A GB 703272A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrrolidylmethylbenzimidazole
- hydrochloride
- residue
- ring
- diamine
- 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
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 N-pyrrolidylmethyl group Chemical group 0.000 abstract 6
- 238000000034 method Methods 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical class CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 abstract 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 abstract 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007265 chloromethylation reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical class CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 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
- C07D235/14—Radicals substituted by nitrogen atoms
-
- 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
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1950SC001391 DE890644C (de) | 1950-03-03 | 1950-03-03 | Verfahren zur Darstellung von Derivaten des Imidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB703272A true GB703272A (en) | 1954-02-03 |
Family
ID=31983835
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB516151A Expired GB703272A (en) | 1950-03-03 | 1951-03-02 | Manufacture of new derivatives of benzimidazole |
| GB516251A Expired GB703273A (en) | 1950-03-03 | 1951-03-02 | Manufacture of new derivatives of imidazole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB516251A Expired GB703273A (en) | 1950-03-03 | 1951-03-02 | Manufacture of new derivatives of imidazole |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH295243A (enrdf_load_stackoverflow) |
| DE (1) | DE890644C (enrdf_load_stackoverflow) |
| FR (1) | FR1056760A (enrdf_load_stackoverflow) |
| GB (2) | GB703272A (enrdf_load_stackoverflow) |
| NL (1) | NL73080C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2129424A (en) * | 1982-08-27 | 1984-05-16 | Pharmaton Sa | Basic acetanilides |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876233A (en) * | 1956-10-29 | 1959-03-03 | Gruenenthal Chemie | 1-(p-halobenzyl)-2-methyl benzimidazoles and salts |
| FR2998697A1 (fr) | 2012-11-23 | 2014-05-30 | Univ Bretagne Sud | Architecture de reseau de neurone, procede d'obtention et programmes correspondants |
| GB201702160D0 (en) | 2017-02-09 | 2017-03-29 | Univ Leeds Innovations Ltd | Inhibitors for use in therapy |
-
0
- NL NL73080D patent/NL73080C/xx active
-
1950
- 1950-03-03 DE DE1950SC001391 patent/DE890644C/de not_active Expired
-
1951
- 1951-02-28 CH CH295243D patent/CH295243A/de unknown
- 1951-03-02 FR FR1056760D patent/FR1056760A/fr not_active Expired
- 1951-03-02 GB GB516151A patent/GB703272A/en not_active Expired
- 1951-03-02 GB GB516251A patent/GB703273A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2129424A (en) * | 1982-08-27 | 1984-05-16 | Pharmaton Sa | Basic acetanilides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB703273A (en) | 1954-02-03 |
| DE890644C (de) | 1954-07-05 |
| CH295243A (de) | 1953-12-15 |
| FR1056760A (enrdf_load_stackoverflow) | 1954-03-02 |
| NL73080C (enrdf_load_stackoverflow) |
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