Dichloromethane → Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate

HRID 1980974ノート

反応式

HRID 1980974 の反応式
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]Cl)=[CH:16][CH:15]=1>CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 110844654-ChlorobenzenesulfenylchlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

生成物 1

HCID 12897034Methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate収率 26.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Methyl pyrrole-3-carboxylate (2.5 g., 20 mmole) was dissolved in 35 ml. of methylene chloride. p-Chlorobenzenesulfenyl chloride (4.0 g., 22 mmoles) was added dropwise over approximately 2 minutes, and the reaction mixture was stirred at room temperature for 1 hour. Two volumes of ether were added, the mixture extracted twice with 20 ml. portions of water and the organic layer evaporated in vacuo. The resulting oil was chromatographed on 100 g. of silica gel with approximately 25 ml. fractions of the ethyl acetate-1/hexane-7 eluant collected. Fractions 19 to 36 were combined and concentrated to yield methyl 5-(4-chlorophenylthio)pyrrole-3-carboxylate (1.4 g., m.p. 122°-124° C.).

後処理

  1. extractionthe mixture extracted twice with 20 ml
  2. customportions of water and the organic layer evaporated in vacuo
  3. customThe resulting oil was chromatographed on 100 g
  4. customfractions of the ethyl acetate-1/hexane-7 eluant collected
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-89eb65ac0fb346ba942834ad13ae9d2b
出典データセット
uspto-grants-1985_04
特許番号
US04511576

反応ノート

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