Phenacyl bromide → HCID 723245、化合物

HRID 1397305ノート

反応式

HRID 1397305 の反応式
[NH2:1][C:2](=[S:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>CCO.CCOC(C)=O>[C:18]1([C:16]2[N:1]=[C:2]([CH2:3][NH:4][C:5](=[O:12])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:13][CH:15]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 6259Phenacyl bromideHCID 3500543N-(2-amino-2-thioxoethyl)benzamide

生成物 1

HCID 723245HCID 723245、化合物収率 88.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of N-(2-amino-2-thioxoethyl)benzamide (300 mg, 1.54 mmol) and 2-bromoacetophenone (305 mg, 1.54 mmol) in EtOH (10 mL) was heated to 80° C. for 2 h. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The concentrated reaction mixture was diluted with EtOAc and the organic layer was washed with H2O and brine, and concentrated under reduced pressure to yield N-((4-phenylthiazol-2-yl)methyl)benzamide (0.4 g, yield 88%) as a white solid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.69 (br s, 1H), 8.04-8.01 (dd, J=7.8 Hz, 1.5 Hz, 2H), 7.99-7.97 (m, 2H), 7.64 (s, 1H), 7.56-7.52 (m, 4H), 7.48-7.44 (m, 2H), 5.34 (d, J=6 Hz, 2H). MS (ESI) m/z: Calculated for C17H14N2OS: 294.08. found: 295.0 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe concentrated reaction mixture
  4. washthe organic layer was washed with H2O and brine
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-05364d0b2daa4ebe822485ced9605b55
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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