Phosgene → 1,3-Bis(cyclohexylmethyl)urea

HRID 396261Notes

Reaction equation

HRID 396261 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 and dried (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
  5. customdried (0.5 Torr)

Sources & evidence

ORD record
ord-d11ef4c2d0e8414bb407a3585e81dca6
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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