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

HRID 388665

反応式

HRID 388665 の反応式
[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]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 7277Diethylaluminum chlorideHCID 66650398HCID 66650398、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-98c2753829224aa6a60b4fb67dad4f58
出典データセット
uspto-grants-2013_02
特許番号
US08377962B2

関連ノート

読み込み中…