Propyl isocyanate → HCID 19071316, compound

HRID 1955635Notes

Reaction equation

HRID 1955635 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[CH:7]1([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1C=CC=CC=1>[CH:7]1([CH2:13][NH:14][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 76688Cyclohexanemethylamine

Product 1

HCID 19071316HCID 19071316, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Propyl isocyanate (Aldrich, 42 mL, 0.442 mol) was added dropwise to a solution of cyclohexanemethylamine (Aldrich, 50.1 g, 0.442 mol) in anhydrous benzene (800 mL) at 0° C. under nitrogen. The solution was then stirred for 15 min before being concentrated in vacuo to a volume of 250 mL. The colorless crystals which formed upon standing at 0° C. were filtered off, washed with hexanes (2×70 mL), and dried (0.5 Torr) to give 1-(cyclohexylmethyl)-3-propylurea (83.90 g, 96%), m.p. 60°-61° C.; 1H-NMR (DMSO-d6) consistent with structure.

Workup

  1. concentrationbefore being concentrated in vacuo to a volume of 250 mL
  2. customThe colorless crystals which formed
  3. customupon standing at 0° C.
  4. filtrationwere filtered off
  5. washwashed with hexanes (2×70 mL)
  6. customdried (0.5 Torr)

Sources & evidence

ORD record
ord-bad25f12772944de858eb386f5260039
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

Loading…