Sulfuryl chloride → methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

HRID 1679114ノート

反応式

HRID 1679114 の反応式
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2].S(Cl)([Cl:17])(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:17])=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 2808565Methyl 2-acetamidothiophene-3-carboxylate

生成物 1

HCID 818981methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of 19.9 parts of methyl 2-acetamidothiophene-3-carboxylate in 200 parts by volume of chloroform, 8.2 parts by volume of sulfuryl chloride is added dropwise at below 30° C. The mixture is stirred at room temperature for 30 minutes and then cooled with ice. To the mixture, about 300 parts by volume of saturated aqueous sodium bicarbonate solution is cautiously added with stirring. The chloroform layer is separated, washed with water and dried over sodium sulfate. Evaporation of the solvent gives methyl 2-acetamido-5-chlorothiophene-3-carboxylate as crystals. Recrystallization from methanol gives needles melting at 110°-110.5° C. This compound is identical with that obtained in Reference Example 17.

後処理

  1. temperaturecooled with ice
  2. stirringwith stirring
  3. customThe chloroform layer is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-a256973dec644f19a6ef27327a501039
出典データセット
uspto-grants-1978_03
特許番号
US04079060

反応ノート

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