Thionyl Chloride → N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide
Reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:6].S(Cl)([Cl:15])=O>N1C=CC=CC=1.ClC(Cl)Cl>[Cl:15][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:6]Participants
Procedure
To a stirred solution of 40 parts of N-(2-hydroxyethyl)-1-methyl-1H-pyrrole-2-carboxamide in 450 parts of trichloromethane is added one drop of pyridine. Then there are added dropwise, during a 30 minutes-period, 28.3 parts of sulfinyl chloride (slightly exothermic reaction: temp. rises from 15° to 25° C). Upon completion, stirring is continued overnight at room temperature. The reaction mixture is evaporated and the residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 15 parts of N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide.
Workup
- customslightly exothermic reaction
- customrises from 15° to 25° C
- customThe reaction mixture is evaporated
- customthe residue is purified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
- customThe pure fractions are collected
- customthe eluent is evaporated
- stirringThe residue is stirred in 2,2'-oxybispropane
- filtrationThe product is filtered off
- customdried
Sources & evidence
- ORD record
- ord-69c7d5d3d5064dc8b102ba1cd8c340da
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031226
Reaction notes
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