Benzyl isocyanate → HCID 9807300, compound

HRID 2305243Notes

Reaction equation

HRID 2305243 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.[CH2:32]([N:39]=[C:40]=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl.CCOC(C)=O>[CH2:32]([NH:39][C:40]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][CH:19]2[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]2[C:9]2[O:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH:26]=1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 18459163HCID 18459163, compound

Product 1

HCID 9807300HCID 9807300, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

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 benzylisocyanate (0.17 ml, 1.36 mmol) at 5° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc, washed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The resulting solid was collected and washed with EtOAc-hexane to give (±)-1-benzyl-3-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenyl}urea (100.7 mg, 69%).

Workup

  1. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe resulting solid was collected
  5. washwashed with EtOAc-hexane

Sources & evidence

ORD record
ord-4c3a4aadcc524ac9bbb0722a4c808374
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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