Thionyl Chloride → N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide

HRID 437653노트

반응식

HRID 437653 반응식
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]

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 21428972N-(2-hydroxyethyl)-1-methyl-1H-pyrrole-2-carboxamide

생성물 1

HCID 21428944N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 6212Chloroform용매

실험 절차

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.

후처리

  1. customslightly exothermic reaction
  2. customrises from 15° to 25° C
  3. customThe reaction mixture is evaporated
  4. customthe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. stirringThe residue is stirred in 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customdried

출처 및 근거

ORD 기록
ord-69c7d5d3d5064dc8b102ba1cd8c340da
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031226

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