Phosgene → 1-Isocyanato-3-(trifluoromethyl)cyclohexane

HRID 1580578Notes

Reaction equation

HRID 1580578 reaction equation
[C:1](Cl)(Cl)=[O:2].[F:5][C:6]([F:15])([F:14])[CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([NH2:13])[CH2:8]1>C1(C)C(C)=CC=CC=1>[F:5][C:6]([F:14])([F:15])[CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([N:13]=[C:1]=[O:2])[CH2:8]1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 162277663-(Trifluoromethyl)cyclohexylamine (cis-and trans-mixture)

Product 1

HCID 212974231-Isocyanato-3-(trifluoromethyl)cyclohexane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 130 parts of phosgene in 450 parts of xylene at 0° to 5°C. is added dropwise a solution of 100 parts of 3-trifluoromethylcyclohexylamine (prepared as in Example 1) in 450 parts of xylene. The reaction mixture is stirred at 0°C. for 1 hour, allowed to come to ambient temperature, and then refluxed 4 hours. The excess phosgene is trapped in a gas scrubber. The xylene is stripped on a rotary evaporator and the residue is distilled under reduced pressure to yield 62.4 parts of 3-trifluoromethylcyclohexyl isocyanate, b.p. 68°-69°C/9mm.

Workup

  1. customto come to ambient temperature
  2. temperaturerefluxed 4 hours
  3. customThe xylene is stripped on a rotary evaporator
  4. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-364ba409cd364093af2fead9dacf15ee
Source dataset
uspto-grants-1976_01
Patent number
US03933815

Reaction notes

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