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Acetyl chloride → N-(2-acetyl-3,5-dimethoxy-phenyl)-4-isopropylthiazole-2-carboxamide

HRID 388665
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HRID 388665 반응식
[Al](Cl)(CC)CC.[C:7](Cl)(=[O:9])[CH3:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]([C:24]2[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[O:23])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1>C(Cl)Cl>[C:7]([C:14]1[C:13]([O:12][CH3:11])=[CH:18][C:17]([O:19][CH3:20])=[CH:16][C:15]=1[NH:21][C:22]([C:24]1[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=1)=[O:23])(=[O:9])[CH3:8]
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참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 7277Diethylaluminum chlorideHCID 66650398N-(3,5-dimethoxy-phenyl)-4-isopropylthiazole-2-carboxamide

생성물 1

HCID 66650681N-(2-acetyl-3,5-dimethoxy-phenyl)-4-isopropylthiazole-2-carboxamide수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of Et2AlCl (1.61 g, 12.04 mmol) in DCM at 0° C. was added acetyl chloride (630 mg, 8.02 mmol). The mixture was stirred at 0° C. for 30 min. Compound 216e (1.23 g, 4.01 mmol) was then added and the reaction mixture was stirred at 80° C. for 90 min. The reaction was poured in ice and DCM was added. The organic layers were separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (EtOAc/DCM) to yield compound 217e as a white solid in 82% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.41 (s, 3H), 1.43 (s, 3H), 2.63 (s, 3H), 3.20-3.27 (m, 1H), 3.89 (s, 3H), 3.90 (s, 3H), 6.27 (d, J=2.30, 1H), 7.19 (s, 1H), 8.12 (d, J=2.30 Hz, 1H).

후처리

  1. stirringthe reaction mixture was stirred at 80° C. for 90 min
  2. additionThe reaction was poured in ice
  3. customThe organic layers were separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (EtOAc/DCM)

출처 및 근거

ORD 기록
ord-98c2753829224aa6a60b4fb67dad4f58
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377962B2

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