N-methoxy-N-methyl-2-phenyl-1,3-thiazole-5-carboxamide → 1-(2-Phenyl-thiazol-5-yl)-propan-1-one

HRID 396395

反応式

HRID 396395 の反応式
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:7]=1)=[O:5].[CH2:18]([Mg]Br)[CH3:19]>O1CCCC1>[C:11]1([C:9]2[S:10][C:6]([C:4](=[O:5])[CH2:18][CH3:19])=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 9921229N-methoxy-N-methyl-2-phenyl-1,3-thiazole-5-carboxamideHCID 178418443HCID 178418443、化合物

生成物 1

HCID 98559161-(2-Phenyl-thiazol-5-yl)-propan-1-one収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 0.32 g (1.3 mmol) of the above-prepared 2-phenyl-thiazole-5-carboxylic acid methoxy-methyl-amide in tetrahydrofuran at room temperature was added 0.34 g (2.6 mmol) of 1M ethyl magnesium bromide in tetrahydrofuran. The reaction mixture was allowed to stir for one hour. The reaction was quenched with aqueous ammonium chloride and partitioned with ethyl acetate. The organic phase was washed once with aqueous ammonium chloride, once with water, once with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 1:19 ethyl acetate:hexanes to give 0.26 g of the title compound (93%). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H) 8.0 (m, 2H) 7.49 (m, 3H) 2.98 (q, 2H) 1.27 (t, 3H).

後処理

  1. customThe reaction was quenched with aqueous ammonium chloride
  2. custompartitioned with ethyl acetate
  3. washThe organic phase was washed once with aqueous ammonium chloride, once with water, once with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel using 1:19 ethyl acetate

出典と根拠

ORDレコード
ord-72e022f3a8f44bb9a816509c3d54aa4f
出典データセット
uspto-grants-2003_08
特許番号
US06608087B1

関連ノート

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