4-(Trifluoromethyl)thiobenzamide → [5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester

HRID 1869283

반응식

HRID 1869283 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[S:11])[NH2:10])=[CH:5][CH:4]=1.[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19](=O)[CH:20](Br)[CH3:21])[CH3:15]>C(O)C>[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=2)[S:11][C:20]=1[CH3:21])[CH3:15]

참가 물질

4

반응물 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

생성물 1

HCID 57986743[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester수율 47.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
170 °C

실험 절차

To a solution of 4-trifluoromethyl-benzene-thioamide (1.845 g, 9 mmol) in ethanol (15 mL, 200 proof) add ethyl-4-bromo-3-oxo-pentanoate (2.07 g, 9 mmol). Seal this solution warm the solution to 170° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 20 min. Cool the resulting solution to room temperature, concentrate under reduced pressure and purify the residue by flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane) and obtain the title compound as a white solid (1.4 g). MS (ESI) m/z 330 (M+H); H1 NMR (CDCl3) δ1.87 (bs, 1H), 2.49 (s, 3H), 4.86 (s, 2H), 7.67 (d, J=8 Hz, 2H), 8.02 (d, J=8 Hz, 2H).

후처리

  1. customSeal this solution
  2. temperatureCool the resulting solution to room temperature
  3. concentrationconcentrate under reduced pressure
  4. custompurify the residue
  5. washby flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane)

출처 및 근거

ORD 기록
ord-06d1549a0fa74443bbd132a5937e5cac
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638539B2

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