Benzyl Alcohol → o-Benzyl-n,n'-diisopropylisourea

HRID 635561Notes

Reaction equation

HRID 635561 reaction equation
[CH:1]([N:4]=[C:5]=[N:6][CH:7]([CH3:9])[CH3:8])([CH3:3])[CH3:2].[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:5](=[N:6][CH:7]([CH3:9])[CH3:8])[NH:4][CH:1]([CH3:3])[CH3:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 12734Diisopropylcarbodiimide

Product 1

HCID 11128254o-Benzyl-n,n'-diisopropylisourea

Conditions

Temperature
0 °C

Procedure

A neat solution of 18.6 mL (15g, 118.8 mmol) of 1,3-diisopropylcarbodiimide and 60 mg (0.6 mmol) of cuprous chloride was placed under a blanket of argon and then cooled to 0° C. in an ice bath. To this reaction mixture was added dropwise (via syringe) 12.9 mL (13.5 g, 124.7 mmol) of benzyl alcohol. The resultant green reaction mixture was allowed to stir at 0° C. overnight, filtered through celite (rinsing with hexane) and the filtrate then Kugelrohr distilled (105° C., 2 mm Hg) to give 2-benzyl-1,3-diisopropyl isourea as a clear, colorless oil. To a solution of 650 mg (4.7 mmol) of 4-hydroxybenzoic acid in 20 mL of tetrahydrofuran was added 1.1 g (4.7 mmol) of 2-benzyl-1,3-diisopropyl isourea. The reaction mixture was allowed to stir at ambient temperature overnight, filtered (rinsing with tetrahydrofuran) and then concentrated in vacuo. Purification by flash chromatography (silica, 25% ethyl acetate in hexane) gave the title compound as a white solid. PMR (CDCl3): δ 5.22 (1 H, s), 5.35 (2 H, s), 6.87 (2 H, d, J=8.8 Hz), 7.34-7.50 (5 H, m), 8.01 (2 H, d, J=8.8 Hz).

Workup

  1. filtrationfiltered through celite (rinsing with hexane)
  2. distillationthe filtrate then Kugelrohr distilled (105° C., 2 mm Hg)

Sources & evidence

ORD record
ord-d15cfc0054dd4f548a4d5725cbe29847
Source dataset
uspto-grants-2001_02
Patent number
US06187950B1

Reaction notes

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