Thiobenzamide → methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

HRID 2300590노트

반응식

HRID 2300590 반응식
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH3:19])[C:12](=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15].CCOC(C)=O.O>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[CH3:19]

참가 물질

5

반응물 3

HCID 683563ThiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22728543Water ethylacetate

생성물 1

HCID 2775646methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 13.13 g (95.7 mmol) of thiobenzamide and 5.0 g (23.9 mmol) of methyl 4-bromo-3-oxo-pentanoate in 25 mL of dry toluene was heated at 90° C. for 5 h. The solution was poured into EtOAc/water and the aqueous phase extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered, and concentrated. The crude oil was purified by silica gel chromatography eluting with hexanes/EtOAc (3/1 to 2/1) to afford 4.14 g (70%) yield) of the title compound as a pale orange-colored oil: 1H NMR (CDCl3, 400 MHz) δ7.97 (m, 2H), 7.11 (m, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.36 (s, 3H).

후처리

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by silica gel chromatography
  7. washeluting with hexanes/EtOAc (3/1 to 2/1)
  8. customto afford 4.14 g (70%)

출처 및 근거

ORD 기록
ord-cf0ac6c23b46432bb0488c8f91d5af47
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498174B1

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