Potassium Carbonate → HCID 66841952, compound

HRID 253332Notes

Reaction equation

HRID 253332 reaction equation
[CH3:1][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+].C(S([O-])=O)O.[Na+]>O.CN(C)C=O>[CH3:1][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

7

Reactant 4

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 23194991HCID 23194991, compoundHCID 23689980Sodium Formaldehyde Sulfoxylate

Product 1

HCID 66841952HCID 66841952, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of 20 g of 2,4-dimethyl-5-mercaptoaniline and 150 ml of N,N-dimethylformamide, 41 g of 2,2,2-trifluoroethyl iodide and 24 g of potassium carbonate were added, and 4 g of Rongalit was further added, followed by stirring at room temperature for 24 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent hexane:ethyl acetate=5:1) to obtain 29 g of 2,4-dimethyl-5-(2,2,2-trifluoroethylthio)aniline.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (eluent hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5c45bd272cda49449898c9d34baf01d7
Source dataset
uspto-grants-2011_01
Patent number
US07872036B2

Reaction notes

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