Phosgene → N-(3,5-Dimethylphenyl)-N-phenylcarbamoyl chloride

HRID 2226035Notes

Reaction equation

HRID 2226035 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:16](Cl)([Cl:18])=[O:17]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]([Cl:18])=[O:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 127551993,5-Dimethyl-N-phenylaniline

Product 1

HCID 18965188N-(3,5-Dimethylphenyl)-N-phenylcarbamoyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 5.5 g (27.9 mmole) of N-(3,5-dimethylphenyl)aniline, 27.9 mL of 1.93M phosgene in toluene and 15 mL of toluene was heated at 90° C. under nitrogen for 2 hours with stirring. The solution was cooled, flushed with nitrogen for 2 hours to remove excess phosgene and concentrated in vacuo to give 7.15 g (99%) of a red oil.

Workup

  1. temperatureThe solution was cooled
  2. customflushed with nitrogen for 2 hours
  3. customto remove excess phosgene
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c46cf70c2f554b9a9763425014c73ee9
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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