p-Toluenesulfonyl isocyanate → 2-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethyl (4-methylphenyl)sulfonylcarbamate

HRID 891064Notes

Reaction equation

HRID 891064 reaction equation
[C:1]1([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=3)[N:10]=[C:9]([C:21]([F:24])([F:23])[F:22])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1([CH3:37])[CH:30]=[CH:29][C:28]([S:31]([N:34]=[C:35]=[O:36])(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH3:37][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35](=[O:36])[O:20][CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([N:11]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][C:9]([C:21]([F:23])([F:24])[F:22])=[N:10]3)=[CH:13][CH:14]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 222445582-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol

Product 1

HCID 867599362-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethyl (4-methylphenyl)sulfonylcarbamateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{4-[5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol (step 1, 158 mg, 0.48 mmol) in dichloromethane (10 ml) was added p-toluenesulfonyl isocyanate (114 mg, 0.58 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) to afford 184 mg (73%) of the title compound as yellow solids: MS (ESI) m/z 530 [M+H]+, 528 [M−H]−, 1H-NMR (CDCl3) δ 7.87-7.80 (3H, m), 7.36-7.09 (10H, m), 6.75 (1H, s), 4.28 (2H, t, J=6.1 Hz), 2.91 (2H, t, J=6.9 Hz), 2.42 (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)

Sources & evidence

ORD record
ord-a9be8d3ce7324d03a773d91059679849
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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