Phenylsulphonyl isocyanate → HCID 9960140, compound

HRID 2305244Notes

Reaction equation

HRID 2305244 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([NH2:31])[CH:28]=[CH:29][CH:30]=4)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32]1([S:38]([N:41]=[C:42]=[O:43])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:32]1([S:38]([NH:41][C:42]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][CH:19]3[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]3[C:9]3[O:10][C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=3)[CH:26]=2)=[O:43])(=[O:39])=[O:40])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 76096Phenylsulphonyl isocyanateHCID 18459163HCID 18459163, compound

Product 1

HCID 9960140HCID 9960140, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenylamine (110 mg, 0.27 mmol) in methylene chloride (3 ml) was added benzenesulfonylisocyanate (0.037 ml, 0.27 mmol) at 5° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was evaporated, and the residue was purified by silica gel column chromatography (methylene chloride-MeOH, 30:1 elution) to give (±)-1-benzenesulfonyl-3-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenyl}urea (159.0 mg, 100%).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by silica gel column chromatography (methylene chloride-MeOH, 30:1 elution)

Sources & evidence

ORD record
ord-a523b66c6a6f43c692c69939678e0ed6
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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