Phosgene → N,N-dioctadecylcarbamoyl chloride

HRID 1579125Notes

Reaction equation

HRID 1579125 reaction equation
[CH2:1]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:38](Cl)([Cl:40])=[O:39]>C1(C)C=CC=CC=1>[CH2:20]([N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:38]([Cl:40])=[O:39])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 66989Dioctadecylamine

Product 1

HCID 3016265N,N-dioctadecylcarbamoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Distearyl carbamoyl chloride was prepared by charging 2.1 kg of toluene into a flask and then simultaneously adding 1.8kg of melted distearyl amine and 0.5 kg of phosgene under agitation at 55°-60°C. The temperature was then raised to 100°C. The reaction was carried out under slight vacuum and reflux. When the conversion was almost 100%, corresponding to a yield of about 1.8 kg distearyl carbamoyl chloride, toluene and phosgene were evaporated.

Workup

  1. temperaturereflux
  2. customcorresponding to a yield of about 1.8 kg distearyl carbamoyl chloride, toluene and phosgene were evaporated

Sources & evidence

ORD record
ord-99b783b1c15e4e119a6794e1b5ce7393
Source dataset
uspto-grants-1976_02
Patent number
US03940519

Reaction notes

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