N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamide → 4-Acetyl-5-chlorothiophene-2-sulfonamide

HRID 1197435ノート

反応式

HRID 1197435 の反応式
C[Li].[CH3:3]COCC.CN(OC)[C:10]([C:12]1[CH:16]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:14][C:13]=1[Cl:21])=[O:11]>C1COCC1>[C:10]([C:12]1[CH:16]=[C:15]([S:17]([NH2:18])(=[O:20])=[O:19])[S:14][C:13]=1[Cl:21])(=[O:11])[CH3:3]

参加物

4

反応物 2

HCID 19106478N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamideHCID 178467906HCID 178467906、化合物

生成物 1

HCID 191064694-Acetyl-5-chlorothiophene-2-sulfonamide収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 1.5M methyllithium/ether (26 mL, 0.039 mol) was added dropwise to a solution of N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamide (3.25 g, 0.011 mol) in dry THF (145 mL) under a nitrogen atmosphere, cooled to -78° C. After two hours, the reaction mixture was poured carefully into ice/dil. HCl and the product was extracted into ethyl acetate. This extract was washed with water and brine, dried (Na2SO4), filtered and evaporated to give 2.82 g of crude solid product. This material was chromatographed on silica gel and eluted with 40% ethyl acetate/hexane to give 1.7 g (74%) of product. Recrystallization from ethyl acetate/hexane gave 1.68 g of product, mp 128°-130° C.

後処理

  1. additionthe reaction mixture was poured carefully into ice/dil
  2. extractionHCl and the product was extracted into ethyl acetate
  3. washThis extract was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give 2.82 g of crude solid product
  8. customThis material was chromatographed on silica gel
  9. washeluted with 40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-a0902973f10e4932823b0ae2b6ca229c
出典データセット
uspto-grants-1994_01
特許番号
US05276025

反応ノート

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