US4110338A
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Product and preparation of 1H-tetrazole-5-thiol derivatives
Assignee: Astellas Pharma Inc
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Filing: 1974-10-29
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Granted: 1978-08-29
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Expires: 1994-10-29
Abstract
Abstract The process for preparation of and the intermediate compounds such as 1H-tetrazole-5-thiol having the formula ##STR1## wherein R 1 is alkyl, aminoalkyl, acylaminoalkyl, aryl, alkoxycarbonylaminoalkyl, halogen-substituted aryl or alkylamino-substituted aryl and R 2 is hydrogen or arakyl, preferably benzyl. The compound is produced by reacting a substituted thiosemicarbazide with an aralkyl chloride, subjecting the resultant compound to diazotization, and reacting the resultant compound with a Friedel Crafts catalyst. Optionally, this may be further hydrolyzed when R 1 is aminoalkyl and/or converted to conventional salts.
Inventors
- 👤 Takashi Kamiya
- 👤 Kunihiko Tanaka
- 👤 Youichi Shiokawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 07:24
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
121 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thiol of the formula: ##STR11## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR12## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR13## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR14## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR15## and when desired, converting the resultant compound (I') into its salt, wherein R 1 ' is alkyl of 1-6 carbon atoms R 2 is aralkyl, and X is a residue of an acid.
Claim 2
Dependent Claim
121 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thiol of the formula: ##STR11## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR12## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR13## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR14## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR15## and when desired, converting the resultant compound (I') into its salt, wherein R 1 ' is alkyl of 1-6 carbon atoms R 2 is aralkyl, and X is a residue of an acid.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein R 2 is phenylethyl X is halogen.
Claim 4
Dependent Claim
13 words
The process of claim 1 wherein R 2 is naphthylmethyl X is halogen.
Claim 5
Dependent Claim
14 words
The process of claim 1 wherein R 2 is benzyl, and X is halogen.
Claim 6
Dependent Claim
18 words
The process of claim 4 wherein R 1 and R 1 ' are methyl, and X is chlorine.
Claim 7
Dependent Claim
121 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thiol of the formula: ##STR16## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR17## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR18## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR19## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR20## and when desired, converting the resultant compound (I') into its salt, wherein R 1 ' is cycloalkyl of 5-6 carbon atoms R 2 is aralkyl, and X is a residue of an acid.
Claim 8
Dependent Claim
121 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thiol of the formula: ##STR16## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR17## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR18## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR19## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR20## and when desired, converting the resultant compound (I') into its salt, wherein R 1 ' is cycloalkyl of 5-6 carbon atoms R 2 is aralkyl, and X is a residue of an acid.
Claim 9
Dependent Claim
205 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thio of the formula: ##STR21## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR22## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR23## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR24## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR25## and when desired, converting the resultant compound (I') into its salt, wherein R 2 is aralkyl, X is a residue of an acid, and R 1 ' is acylaminoalkyl wherein alkyl is of 1-6 carbon atoms, and acyl is alkanoyl of 1-7 carbon atoms, benzoyl, toluoyl, xyloyl, nicotinoyl, thenoyl or furoyl and, when desired, followed by hydrolyzing the resultant compound (I') to give a compound of the formula: ##STR26## and further, when desired, followed by reacting the resultant compound (I") with a reagent being capable of introducing an alkoxycarbonyl group on the amino group to give a compound of the formula: ##STR27## and furthermore, when desired, converting the resultant compound (I'), (I") or (I''') into its salt.
Claim 10
Dependent Claim
205 words
A process for the preparation of a 1-substituted 1H-tetrazole-5-thio of the formula: ##STR21## which comprises reacting at elevated temperature a substituted thiosemicarbazide of the formula: ##STR22## with a compound of the formula: R.sub.2 --X (III) to give a N,S-disubstituted thiosemicarbazine of the formula: ##STR23## subjecting at lower temperature the resultant compound (IV) to diazotization to give a 5-aralkylthio-1H-tetrazole of the formula: ##STR24## and reacting at elevated temperature the resultant compound (V) with a slightly molar excess of Friedel Crafts' catalyst to give a compound of the formula: ##STR25## and when desired, converting the resultant compound (I') into its salt, wherein R 2 is aralkyl, X is a residue of an acid, and R 1 ' is acylaminoalkyl wherein alkyl is of 1-6 carbon atoms, and acyl is alkanoyl of 1-7 carbon atoms, benzoyl, toluoyl, xyloyl, nicotinoyl, thenoyl or furoyl and, when desired, followed by hydrolyzing the resultant compound (I') to give a compound of the formula: ##STR26## and further, when desired, followed by reacting the resultant compound (I") with a reagent being capable of introducing an alkoxycarbonyl group on the amino group to give a compound of the formula: ##STR27## and furthermore, when desired, converting the resultant compound (I'), (I") or (I''') into its salt.
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) | 1981-08-28 | 1982-02-27 | 1982-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-28 | 1986-02-27 | 1986-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-28 | 1990-02-27 | 1990-08-29 | $7700.00 | Window Closed / Lapsed |