Benzyl mercaptan → 5-(2-Benzylthio-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

HRID 1178600ノート

反応式

HRID 1178600 の反応式
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:12]1[CH:17]=[C:16]([C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>CCCCCC.CN(C)C=O>[CH2:9]([S:10][C:12]1[CH:17]=[C:16]([C:18]2[S:22][C:21]([C:23]3[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=3)=[N:20][C:19]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[CH:15]=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 102739295-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

生成物 1

HCID 219642205-(2-Benzylthio-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole収率 79%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

実験手順

After sodium hydride (60% paraffin dispersion, 0.13 g, 3.2 mmol) was washed with hexane twice, it was suspended in N,N-dimethylformamide (15 mL). Phenylmethanethiol (0.35 mL, 3.0 mmol) was added to this suspension and stirred for 10 minutes. A solution of 5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole (0.49 g, 1.2 mmol) in N,N-dimethylformamide (5 mL) was added to this mixture and stirred for 1 hour. An 8N aqueous solution of sodium hydroxide was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate, and the extract was washed with water. This extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1) to obtain 0.48 g (yield 79%).

後処理

  1. stirringstirred for 1 hour
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customThis extract was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1)
  7. customto obtain 0.48 g (yield 79%)

出典と根拠

ORDレコード
ord-9b0f22c755b74203868470e05536e303
出典データセット
uspto-grants-2007_10
特許番号
US07276527B2

反応ノート

読み込み中…