Ammonia → 4-(4-Fluorophenyl)-2-methylthiazole

HRID 875017ノート

反応式

HRID 875017 の反応式
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O.N>C(O)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:4]=[C:1]([CH3:2])[S:3][CH:6]=2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 222AmmoniaHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2723949Thioacetamide

生成物 1

HCID 7318944-(4-Fluorophenyl)-2-methylthiazole収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Thioacetamide (1.73 g, 23.03 mmol) was added to a solution of 2-bromo-1-(4-fluorophenyl)ethanone (5.0 g, 23.03 mmol) in ethanol (50 mL) and the reaction was refluxed at 70° C. for 4 h. The reaction mixture was then cooled to room temperature, neutralized to pH 7 with aqueous ammonia solution (20 ml), and extracted with ethyl acetate (200 mL). The combined extracts were washed with water (100 mL), dried over Na2SO4, and concentrated to provide 4-(4-fluorophenyl)-2-methylthiazole (4.0 g, 90%). 1H NMR (400 MHz, DMSO) δ 7.95-8.00 (m, 2H), 7.91 (s, 1H), 7.23-7.29 (m, 2H), 2.71 (s, 3H). MS (ESI) m/z: Calculated for C10H8FNS: 193.04. found: 194.0 (M+H)+

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe combined extracts were washed with water (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8b3707a9691147f7957423ee55727c56
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

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