4-Methoxybenzyl alcohol → O-p-methoxybenzyl-N,N'-diisopropylisourea

HRID 234820Notes

Reaction equation

HRID 234820 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[CH:11]([N:14]=[C:15]=[N:16][CH:17]([CH3:19])[CH3:18])([CH3:13])[CH3:12]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:15](=[N:14][CH:11]([CH3:13])[CH3:12])[NH:16][CH:17]([CH3:19])[CH3:18])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 12734Diisopropylcarbodiimide

Product 1

HCID 10563595O-p-methoxybenzyl-N,N'-diisopropylisourea

Conditions

Temperature
60 °C

Procedure

Anhydrous cupric chloride (8 mg) is added to a mixture of 4-methoxybenzyl alcohol (2.76 g) and 1,3-diisopropylcarbodiimide (3.13 mL) under a nitrogen atmosphere. The reaction is quite exothermic and it is cooled with an ice bath for 1 h. The mixture is then heated for 3.5 h at 60° C. The product was purified by distillation to give O-p-methoxybenzyl-N,N'-diisopropylisourea (4 g).

Workup

  1. temperatureit is cooled with an ice bath for 1 h
  2. distillationThe product was purified by distillation

Sources & evidence

ORD record
ord-6e4ebd88908e4df2ad25ca4b58874d39
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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