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

HRID 891076노트

반응식

HRID 891076 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d38ab3e84a74d57adf7479197e3b70a
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001917B2

반응 노트

불러오는 중…