Ethanol → Ethyl 3-(4-phenylthiazol-2-yl)propanoate

HRID 1397332노트

반응식

HRID 1397332 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12](=[S:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[CH3:20]CO>>[C:5]1([C:3]2[N:11]=[C:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:20])=[O:16])[S:19][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

4

반응물 3

HCID 702EthanolHCID 6259Phenacyl bromideHCID 18333020Methyl 4-amino-4-thioxobutanoate

생성물 1

HCID 67325597Ethyl 3-(4-phenylthiazol-2-yl)propanoate수율 40%

반응 조건

온도
80 °C

실험 절차

A mixture of 2-bromo acetophenone (2.1 g, 10.55 mmol) and methyl 4-amino-4-thioxobutanoate (1.6 g, 10.86 mmol) in EtOH (15 mL) was heated to 80° C. for 3 h. Reaction mixture was cooled to room temperature and solvent was evaporated under reduced pressure. The product was extracted with EtOAc and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford ethyl 3-(4-phenylthiazol-2-yl)propanoate (1.1 g, yield 40%) as a white solid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.44-7.39 (m, 2H), 7.35-7.30 (m, 2H), 4.22-4.15 (q, J=7.2 Hz, 2H), 3.41-3.36 (t, J=7.5 Hz, 2H), 2.94-2.89 (t, J=7.3 Hz, 2H), 1.30-1.25 (t, J=7.1 Hz, 3H). MS (ESI) m/z: Calculated for C14H15NO2S: 261.08. found: 262.2 (M+H)+.

후처리

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customsolvent was evaporated under reduced pressure
  4. extractionThe product was extracted with EtOAc
  5. washthe organic layer was washed with H2O and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-127a4d1b04454c45bdbc1465da020fdf
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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