Phosgene → N-methyl-N-[2-(trifluoromethyl)phenyl]carbamoyl chloride

HRID 1033812Notes

Reaction equation

HRID 1033812 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[C:13](Cl)([Cl:15])=[O:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:10])([F:11])[F:12])[C:13]([Cl:15])=[O:14]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 27608942-Trifluoromethyl-N-methylaniline

Product 1

HCID 19024472N-methyl-N-[2-(trifluoromethyl)phenyl]carbamoyl chlorideYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1.00 g (5.71 mmole) of 2-(methylamino)benzotrifluoride, 9 mL (17.3 mmole) of 1.93M phosgene in toluene, and 10 mL of toluene was stirred under N2 for a hour and then treated with 20 mL of 2.5N sodium hydroxide (aqueous). The layers were separated, and the organic phase was concentrated in vacuo to yield 1.12 g (83%) of the title compound as a clear oil, which eventually solidified after prolonged standing: mp 44°-46° C.; homogeneous by TLC in 3:1 hexane-EtOAc; IR spectrum νCO 1750 cm-1 ; FAB-MS m/e 237 (M+1)+.

Workup

  1. customThe layers were separated
  2. concentrationthe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-017eaa8841e04cedb6cc80e0d50689c4
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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