Phosgene → 1,3-Bis(cyclohexylmethyl)urea

HRID 2304819Notes

Reaction equation

HRID 2304819 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:11](Cl)(Cl)=[O:12]>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][NH:8][C:11]([NH:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 76688Cyclohexanemethylamine

Product 1

HCID 2315151,3-Bis(cyclohexylmethyl)ureaYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of cyclohexanemethylamine (Aldrich, 68.66 g) and 5 N sodium hydroxide (Fisher, 200 ml) was stirred vigorously with cooling (−10° C.) while a solution of phosgene (30.0 g) in toluene (600 ml) was added rapidly. After stirring for 20 minutes, the resulting mixture was filtered and the precipitated solid was washed with water (˜1500 ml) and dried at 67 Pa (0.5 Torr) to give 1,3-bis(cyclohexylmethyl)urea as white powder (72.72 g, 95%), m.p. 150-152° C.; 1H-NMR (DMSO-d6) δ: 5.74 (br t, J=5.8 Hz, 2, 2 NH), 2.81 (t, J=6.3 Hz, 4, 2 NCH2), 1.62, 1.25, and 0.85 (all m, 22, 2 cyclohexyl).

Workup

  1. additionwas added rapidly
  2. stirringAfter stirring for 20 minutes
  3. filtrationthe resulting mixture was filtered
  4. washthe precipitated solid was washed with water (˜1500 ml)
  5. customdried at 67 Pa (0.5 Torr)

Sources & evidence

ORD record
ord-0225fd040536497e82d341015a9725d0
Source dataset
uspto-grants-2002_08
Patent number
US06437124B1

Reaction notes

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