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Ethanol → 3-Thiazol-4-yl-benzoic acid methyl ester

HRID 1265611
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HRID 1265611 반응식
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])=O.[CH:14]([NH2:16])=[S:15].[CH3:17]CO>>[CH3:17][O:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([C:3]2[N:16]=[CH:14][S:15][CH:2]=2)[CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 702EthanolHCID 27568353-(Bromoacetyl)benzoic acidHCID 3005587Methanethioamide

생성물 1

HCID 696880593-Thiazol-4-yl-benzoic acid methyl ester

실험 절차

A solution of 3-(2-bromo-acetyl)-benzoic acid (1.22 g) and thioformamide (0.46 g) in EtOH (5 mL) was heated to 80° C. for 1 h. The mixture was partitioned between AcOEt and brine and the organic layer was dried and evaporated. The residual oil was dissolved in a mixture of MeOH (20 mL) and 4NHCl/Et2O (5 mL). After being kept at 20° C. for 18 h, the solution was concentrated in vacuum, diluted with AcOEt, washed with sat. NaHCO3 solution and brine, dried and evaporated. The residue was chromatographed on silica gel using AcOEt/hexane (1:3) as eluent to give 3-thiazol-4-yl-benzoic acid methyl ester (0.98 g) as off-white solid, MS (ISP) 220.2 [(M+H)+].

후처리

  1. customThe mixture was partitioned between AcOEt and brine
  2. customthe organic layer was dried
  3. customevaporated
  4. dissolutionThe residual oil was dissolved in a mixture of MeOH (20 mL)
  5. concentrationthe solution was concentrated in vacuum
  6. additiondiluted with AcOEt
  7. washwashed with sat. NaHCO3 solution and brine
  8. customdried
  9. customevaporated
  10. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-0e5bb50fdc0a4472908fd6afad97d366
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06544985B2

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