Dimethylformamide → 1-(2-chloroethyl)-1,4-dihydro-4-[2-(2-thienyl)ethyl]-5H-tetrazol-5-one
Reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)(=O)=O)=CC=1.[Cl:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[NH:25][N:24]=[N:23]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[Cl:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[N:25]([CH2:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[N:24]=[N:23]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 19.6 parts of [2-(2-thienyl)ethyl] 4-methylbenzenesulfonate, 10 parts of 1-(2-chloroethyl)-1,4-dihydro-5H-tetrazol-5-one, 10 parts of sodium carbonate and 90 parts of N,N-dimethylformamide is stirred and heated overnight at 70° C. The reaction mixture is cooled, 100 parts of water are added and the product is extracted three times with methylbenzene. The combined extracts are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and petroleumether (70:30 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 15 parts (46.5%) of 1-(2-chloroethyl)-1,4-dihydro-4-[2-(2-thienyl)ethyl]-5H-tetrazol-5-one as a residue.
Workup
- temperatureThe reaction mixture is cooled
- extractionthe product is extracted three times with methylbenzene
- customThe combined extracts are dried
- filtrationfiltered
- customevaporated
- customThe residue is purified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and petroleumether (70:30 by volume) as eluent
- customThe pure fractions are collected
- customthe eluent is evaporated
Sources & evidence
- ORD record
- ord-ad396ef9be6d4c6ca56c4eb5415ac18b
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04167574
Reaction notes
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