Phosgene → 2,6-Diethyl-4-nitrophenylisocyanate

HRID 26024Notes

Reaction equation

HRID 26024 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([C:7]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([CH2:17][CH3:18])[C:8]=1[NH2:9])[CH3:6]>C1(C)C=CC=CC=1>[CH2:17]([C:10]1[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=[C:7]([CH2:5][CH3:6])[C:8]=1[N:9]=[C:1]=[O:2])[CH3:18]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 81426772,6-Diethyl-4-nitroaniline

Product 1

HCID 203836312,6-Diethyl-4-nitrophenylisocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Excess phosgene is bubbled into a warm solution of 21.5 g (0.11 moles) of 2,6-diethyl-4-nitroaniline in toluene (250 ml). After the addition, the mixture is heated to reflux and approximately 200 ml of toluene are distilled. The remainder of the toluene is removed under vacuum and the remaining brown semi-solid is distilled under vacuum to give 2,6-diethyl-4-nitrophenylisocyanate, b.p. 135°-144° C./1 mm, as a yellow liquid which crystallized on standing.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux
  4. distillationapproximately 200 ml of toluene are distilled
  5. customThe remainder of the toluene is removed under vacuum
  6. distillationthe remaining brown semi-solid is distilled under vacuum

Sources & evidence

ORD record
ord-f7fe7bcfb4234004b8032086d9231bf4
Source dataset
uspto-grants-1979_04
Patent number
US04147804

Reaction notes

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