2,4-Difluoroaniline → phenyl N-(2,4-difluorophenyl)carbamate

HRID 1731842Notes

Reaction equation

HRID 1731842 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12]>C1(C)C=CC=CC=1>[C:14]1([O:13][C:11](=[O:12])[NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[F:1])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 15891Phenyl chloroformate

Product 1

HCID 13733129phenyl N-(2,4-difluorophenyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.94 g of 2,4-difluoroaniline in 20 ml of toluene was added dropwise 1.29 g of phenyl chloroformate. The mixture was stirred for 15 minutes, washed with three 10 ml portions of water, dried over anhydrous sodium sulfate, and filtered through a pad of diatomaceous earth. The filtrate was evaporated in vacuo to give an oil which solidified on cooling. The solid was crystallized from hexane to give 1.73 g of the desired product as pale tan crystals in 93% yield, mp 82°-84° C.

Workup

  1. washwashed with three 10 ml portions of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered through a pad of diatomaceous earth
  4. customThe filtrate was evaporated in vacuo
  5. customto give an oil which
  6. temperatureon cooling
  7. customThe solid was crystallized from hexane

Sources & evidence

ORD record
ord-bb837270ff174b00a030cedeffda7f59
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

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