Phenyl isocyanate → 1-Cyclohexyl-4,4-dimethyl-3-phenylcarbamoyloxy-2-(1,2,4-triazol-1-yl)-pent-1-ene

HRID 579711Notes

Reaction equation

HRID 579711 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]1([CH:16]=[C:17]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH:18]([OH:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C([O-])(=O)CCCCCCCCCCC.C([Sn+](CCCC)CCCC)CCC.CCOCC>[CH:10]1([CH:16]=[C:17]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH:18]([O:23][C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 1148141-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol

Product 1

HCID 541457961-Cyclohexyl-4,4-dimethyl-3-phenylcarbamoyloxy-2-(1,2,4-triazol-1-yl)-pent-1-eneYield 25.1%

Reagents, catalysts & solvents 2

HCID 21873087Tributyl-tin laurateCatalystHCID 3283Diethyl EtherSolvent

Procedure

6.5 g (0.055 mol) of phenyl isocyanate and three drops of tributyl-tin laurate, as the catalyst, were added to a solution of 13.15 g (0.05 mol) of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol (Example 2) in 100 ml of ether. The mixture was stirred at room temperature for 5 days. After distilling off the solvent in vacuo, the residue was recrystallised from ethyl acetate/ligroin. 4.8 g (25.1% of theory) of 1-cyclohexyl-4,4-dimethyl-3-phenylcarbamoyloxy-2-(1,2,4-triazol-1-yl)-pent-1-ene of melting point 156° C. were obtained.

Workup

  1. distillationAfter distilling off the solvent in vacuo
  2. customthe residue was recrystallised from ethyl acetate/ligroin

Sources & evidence

ORD record
ord-c3d0e38f22bc4020995909fa9509ff3f
Source dataset
uspto-grants-1988_06
Patent number
US04749405

Reaction notes

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