Phosgene → Carbamic chloride, N-methyl-N-phenyl-

HRID 345464Notes

Reaction equation

HRID 345464 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9](Cl)([Cl:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9]([Cl:11])=[O:10]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 7515N-MethylanilineHCID 11430Potassium Carbonate

Product 1

HCID 77969Carbamic chloride, N-methyl-N-phenyl-Yield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

A vigorously stirred solution of 10.7 g (0.1 mole) of N-methylaniline in 100 ml of acetonitrile was added dropwise under a nitrogen atmosphere to a cold mixture of 155 ml (0.3 mole) of a 1.93M solution of phosgene in toluene and 83.0 g (0.6 mole) of anhydrous potassium carbonate in 200 ml of acetonitrile. After the final addition, the mixture was stirred at ambient temperature for 16 h, filtered, and the filtrate concentrated under reduced pressure. The residue was recrystallized from benzene/petroleum ether (60°-110° C.) to yield 15.9 g (94%) of white solid, mp 85°-86° C.

Workup

  1. additionAfter the final addition
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was recrystallized from benzene/petroleum ether (60°-110° C.)

Sources & evidence

ORD record
ord-6bf4d4a814ba4dfd831563a9cd6d49b7
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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