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US4380635A
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Synthesis of acylated benzothiophenes
Assignee: Eli Lilly and Co
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Filing: 1981-12-16
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Granted: 1983-04-19
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Expires: 2001-12-16
Abstract
Abstract A group of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)benzoyl]benzo[b]thiophenes are prepared by acylation of a methyl-protected starting compound followed by demethylation in a single reaction mixture.
Inventors
- 👤 Mary K. Peters
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:49
CPC Classifications
C; C07; C07C; C07C323/00; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
128 words
A process for preparing a compound of the formula ##STR4## wherein R 1 and R 2 are independently C 1 -C 4 alkyl, or combine to form C 4 -C 6 polymethylene, --CH 2 CH(CH 3 )CH 2 CH 2 -- or --(CH 2 ) 2 O(CH 2 ) 2 --; which process comprises acylating a compound of the formula ##STR5## in the presence of aluminum chloride or aluminum bromide with an acylating agent of the formula ##STR6## wherein R 4 is chloro or bromo; and adding to the reaction mixture a sulfur compound chosen from the group consisting of methionine and compounds of the formula X--S--Y wherein X is hydrogen or unbranched C 1 -C 4 alkyl, and Y is C 1 -C 4 alkyl or phenyl.
Claim 2
Dependent Claim
128 words
A process for preparing a compound of the formula ##STR4## wherein R 1 and R 2 are independently C 1 -C 4 alkyl, or combine to form C 4 -C 6 polymethylene, --CH 2 CH(CH 3 )CH 2 CH 2 -- or --(CH 2 ) 2 O(CH 2 ) 2 --; which process comprises acylating a compound of the formula ##STR5## in the presence of aluminum chloride or aluminum bromide with an acylating agent of the formula ##STR6## wherein R 4 is chloro or bromo; and adding to the reaction mixture a sulfur compound chosen from the group consisting of methionine and compounds of the formula X--S--Y wherein X is hydrogen or unbranched C 1 -C 4 alkyl, and Y is C 1 -C 4 alkyl or phenyl.
Claim 3
Dependent Claim
24 words
A process of claim 1 wherein the product and the acylating agent are compounds wherein R 1 and R 2 combine to form tetramethylene.
Claim 4
Dependent Claim
24 words
A process of claim 1 wherein the product and the acylating agent are compounds wherein R 1 and R 2 combine to form pentamethylene.
Claim 5
Dependent Claim
32 words
A process of claim 1 wherein the product and the acylating agent are compounds wherein R 1 and R 2 combine to form --CH 2 CH(CH 3 )CH 2 CH 2 --.
Claim 6
Dependent Claim
14 words
A process of any one of claims 1-4 wherein the catalyst is aluminum chloride.
Claim 7
Dependent Claim
20 words
A process of any one of claims 1-4 wherein the acylating agent is a compound wherein R 4 is chloro.
Claim 8
Dependent Claim
17 words
A process of claim 5 wherein the acylating agent is a compound wherein R 4 is chloro.
Claim 9
Dependent Claim
21 words
A process of any one of claims 1-4 wherein to the reaction mixture is added a C 1 -C 4 alkylthiol.
Claim 10
Dependent Claim
10 words
A process of claim 8 wherein the alkylthiol is ethanethiol.
Claim 11
Dependent Claim
18 words
A process of claim 5 wherein to the reaction mixture is added a C 1 -C 4 alkylthiol.
Claim 12
Dependent Claim
10 words
A process of claim 10 wherein the alkylthiol is ethanethiol.
Claim 13
Dependent Claim
18 words
A process of claim 7 wherein to the reaction mixture is added a C 1 -C 4 alkylthiol.
Claim 14
Dependent Claim
10 words
A process of claim 12 wherein the alkylthiol is ethanethiol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-04-18 | 1986-10-18 | 1987-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-18 | 1990-10-18 | 1991-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-18 | 1994-10-18 | 1995-04-19 | $7700.00 | Window Closed / Lapsed |