p-Toluenesulfonyl isocyanate → 2-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethyl (4-methylphenyl)sulfonylcarbamate mono-ammonium salt

HRID 891076ノート

反応式

HRID 891076 の反応式
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[C:5]([CH3:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=2)[N:3]=1.[C:24]1([CH3:36])[CH:29]=[CH:28][C:27]([S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[NH4+:3].[CH3:36][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][C:34](=[O:35])[O:23][CH2:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([N:4]3[C:5]([CH3:14])=[C:6]([C:7]4[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=4)[C:2]([CH3:1])=[N:3]3)=[CH:20][CH:19]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 222445852-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

生成物 1

HCID 865909132-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethyl (4-methylphenyl)sulfonylcarbamate mono-ammonium salt収率 67.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-{4-[3,5-dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol (step 1, 0.88 mmol) in dichloromethane (10 ml) was added p-toluenesulfonyl isocyanate (221 mg, 1.06 mmol). The resulting mixture was stirred at room temperature for 30 min. The reaction mixture washed with water and the organic phase was dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with toluene/ethanol (10:1) and SCX eluting with 2 M NH3 methanol solution to afford 155 mg (35%) of the title compound as white solids: MS (ESI) m/z 545 [M+H]+, 543 [M−H]−, 1H-NMR [DMSO-d6 (dimethyl-d6 sulfoxide)]δ 7.48 (2H, d, J=8.1 Hz), 7.32-7.20 (4H, m), 7.27-7.10 (4H, m), 7.07-7.04 (2H, d, J=8.1 Hz), 3.80 (2H, t, J=6.8 Hz), 2.69 (2H, t, J=6.8 Hz), 2.23 (3H, s), 2.19 (3H, s), 2.14 (3H, s), 2.09 (3H, s).

後処理

  1. washThe reaction mixture washed with water
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. customAfter removal of the solvent
  4. customthe crude product was purified by TLC with toluene/ethanol (10:1) and SCX
  5. washeluting with 2 M NH3 methanol solution

出典と根拠

ORDレコード
ord-4d38ab3e84a74d57adf7479197e3b70a
出典データセット
uspto-grants-2006_02
特許番号
US07001917B2

反応ノート

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