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

HRID 1197435노트

반응식

HRID 1197435 반응식
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]

참가 물질

4

반응물 2

HCID 19106478N-methyl-N-methoxy-2-chloro-5-sulfamoylthiophene-3-carboxamideHCID 178467906HCID 178467906, 화합물

생성물 1

HCID 191064694-Acetyl-5-chlorothiophene-2-sulfonamide수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0902973f10e4932823b0ae2b6ca229c
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276025

반응 노트

불러오는 중…