p-Toluenesulfonyl isocyanate → 2-[4-(2-Amino-5-methyl-4-phenyl-1H-imidazol-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 967811ノート

反応式

HRID 967811 の反応式
[NH2:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=2)[C:4]([CH3:13])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:23]1([CH3:35])[CH:28]=[CH:27][C:26]([S:29]([N:32]=[C:33]=[O:34])(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:35][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:33](=[O:34])[O:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([N:3]3[C:4]([CH3:13])=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:6]=[C:2]3[NH2:1])=[CH:19][CH:18]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 222913562-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol

生成物 1

HCID 865903002-[4-(2-Amino-5-methyl-4-phenyl-1H-imidazol-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate収率 4.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-[4-(2-amino-5-methyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethanol (100 mg, 0.34 mmol) and p-toluenesulfonylisocyanate (67 mg, 0.34 mmol) in dichloromethane (5 mL) was stirred at 0° C. for 10 min. It was washed with water and organic phase was dried over Na2SO4. After removal of solvent, the residue was purified by TLC with dichloromethane/methanol (10:1) to afford 8 mg (4.8%) of the title compound as white solids: MS (ESI) m/z 491 [M+H]+, 489 [M−H]−, 1H-NMR (CDCl3) δ 2.27 (s, 3H), 2.87 (2H, t, J=5.9 Hz), 3.50 (3H, s), 4.24 (2H, t, J=5.7 Hz), 7.56-7.15 (11H, m), 7.83-7.80 (2H, m).

後処理

  1. washIt was washed with water and organic phase
  2. dry with materialwas dried over Na2SO4
  3. customAfter removal of solvent
  4. customthe residue was purified by TLC with dichloromethane/methanol (10:1)

出典と根拠

ORDレコード
ord-285b0dd33ba04319ab5b2bce40b71266
出典データセット
uspto-grants-2005_10
特許番号
US06956050B2

反応ノート

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