GB820476A - 5-dibenzo [b.f.] azepines and their preparation - Google Patents
5-dibenzo [b.f.] azepines and their preparationInfo
- Publication number
- GB820476A GB820476A GB35147/57A GB3514757A GB820476A GB 820476 A GB820476 A GB 820476A GB 35147/57 A GB35147/57 A GB 35147/57A GB 3514757 A GB3514757 A GB 3514757A GB 820476 A GB820476 A GB 820476A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iminodibenzyl
- acetyl
- iminostilbene
- dichloro
- bromo
- 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
- 150000001538 azepines Chemical class 0.000 title 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 7
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 3
- 239000012346 acetyl chloride Substances 0.000 abstract 3
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- QBSUAHGUFKVVTM-UHFFFAOYSA-N 1-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 QBSUAHGUFKVVTM-UHFFFAOYSA-N 0.000 abstract 1
- BQJOARHHFRKHHR-UHFFFAOYSA-N 1-[4-imino-3-(2-phenylethenyl)cyclohexa-1,5-dien-1-yl]ethanone Chemical compound C(C)(=O)C=1C=CC(C(C1)C=CC1=CC=CC=C1)=N BQJOARHHFRKHHR-UHFFFAOYSA-N 0.000 abstract 1
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 abstract 1
- -1 5-carbethoxy-iminodibenzyl Chemical group 0.000 abstract 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 abstract 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- LRIMCLUSKSFCLB-UHFFFAOYSA-N ethyl 4-imino-3-(2-phenylethenyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound C(=O)(OCC)C=1C=CC(C(C1)C=CC1=CC=CC=C1)=N LRIMCLUSKSFCLB-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical group COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0820476/IV (a)/1> (wherein X is a hydrogen or halogen atom, or a methyl group), and the preparation thereof by acylating (e.g. with acetyl chloride, chloroformic acid methyl or ethyl ester) a 10 : 11 dihydro-5-dibenzo [b.f.] azepine (iminodibenzyl), then reacting the 5-acyl derivative with a halogenating agent (e.g. N-bromo- or N-chloro-succinimide or N-bromo-acetamide or -phthalimide) and treating the resulting 5-acyl-10-halogen-10 : 11-dihydro-5-dibenzo [b.f.] azepine with a dehydrohalogenating agent and simultaneously or subsequently hydrolysing with an alkali metal hydroxide or tertiary organic base (e.g. collidine). In Example (1), iminodibenzyl is treated with acetyl chloride, N-bromosuccinimide, then dehydrobrominated and hydrolysed to iminostilbene. Similarly made is 3 : 7-dichloro-iminostilbene. 2 : 8-Dichloro-, 1 : 9-dichloro-, 3 : 7-dimethyl-, 2 : 8-dimethyl-, and 1 : 9-dimethyliminodibenzyl are also suitable starting materials. 5-Acetyl-iminostilbene is made by dehydrobrominating 10 - bromo - 5 - acetyl - iminodibenzyl, which is made by reacting N-bromo-succinimide with 5-acetyl-iminodibenzyl, itself made from iminodibenzyl and acetyl chloride. Similarly made are 5-acetyl-3 : 7-dichloro-iminostilbene and 5 - aceto - 3 : 7 - dichloro - iminodibenzyl. 5 - Carbethoxy-iminostilbene is made by dehydrobrominating 10 - bromo - 5 - carbethoxy - iminodibenzyl, which is made by reacting N-bromosuccinimide with 5-carbethoxy-iminodibenzyl, itself made from iminodibenzyl and chloroformic acid ethyl ester.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH820476X | 1956-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB820476A true GB820476A (en) | 1959-09-23 |
Family
ID=4539388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35147/57A Expired GB820476A (en) | 1956-11-13 | 1957-11-12 | 5-dibenzo [b.f.] azepines and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB820476A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178406A (en) * | 1965-04-13 | Nitrates of s-acymminoimbenzyls | ||
| CN103288737A (en) * | 2013-06-03 | 2013-09-11 | 常州大学 | Synthesis method of iminostilbene |
-
1957
- 1957-11-12 GB GB35147/57A patent/GB820476A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178406A (en) * | 1965-04-13 | Nitrates of s-acymminoimbenzyls | ||
| CN103288737A (en) * | 2013-06-03 | 2013-09-11 | 常州大学 | Synthesis method of iminostilbene |
| CN103288737B (en) * | 2013-06-03 | 2015-08-26 | 常州大学 | A kind of synthetic method of iminostilbene |
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