Potassium Carbonate → 2-Chloro-4-methyl-5-(2,2,2-trifluoroethylthio)aniline

HRID 253319Notes

Reaction equation

HRID 253319 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([SH:10])=[CH:5][C:3]=1[NH2:4].[F:11][C:12]([F:16])([F:15])[CH2:13]I.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10][CH2:13][C:12]([F:16])([F:15])[F:11])=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 668424682-Chloro-4-methyl-5-mercaptoaniline

Product 1

HCID 668419482-Chloro-4-methyl-5-(2,2,2-trifluoroethylthio)anilineYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.4 g of 2-chloro-4-methyl-5-mercaptoaniline, 20 g of 2,2,2-trifluoroethyl iodide, 13 g of potassium carbonate and 200 ml of N,N-dimethylformamide was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with toluene. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 13.5 g of 2-chloro-4-methyl-5-(2,2,2-trifluoroethylthio)aniline.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with toluene
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f485710427ad48aaa160f68ce41664b0
Source dataset
uspto-grants-2011_01
Patent number
US07872036B2

Reaction notes

Loading…