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

HRID 891076Notes

Reaction equation

HRID 891076 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4d38ab3e84a74d57adf7479197e3b70a
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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