Dimethyl Sulfoxide → 2-Amino-3-nitro-6-(2-chloro-4-trifluoromethylphenoxy)pyridine

HRID 2412525Notes

Reaction equation

HRID 2412525 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[NH2:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16](Cl)[N:15]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[NH2:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([O:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[Cl:1])[N:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 27366032-Chloro-4-(trifluoromethyl)phenol

Product 1

HCID 133426282-Amino-3-nitro-6-(2-chloro-4-trifluoromethylphenoxy)pyridineYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.5 g of 2-chloro-4-trifluoromethylphenol, 10.0 g of 2-amino-3-nitro-6-chloropyridine, 10.5 g of potassium carbonate, and 200 ml of dimethyl sulfoxide were charged in a flask, and the mixture was allowed to react at 30° C. for twenty-four hours while stirring. After completion of the reaction, the reaction product was poured into water, followed by extracting with methylene chloride. The extracted phase was washed with water and dried, and the methylene chloride was distilled off under reduced pressure to obtain 14.7 g of a titled compound having a melting point of 80° to 84° C.

Workup

  1. customto react at 30° C. for twenty-four hours
  2. customAfter completion of the reaction
  3. extractionby extracting with methylene chloride
  4. washThe extracted phase was washed with water
  5. customdried
  6. distillationthe methylene chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-703b9a2eefa24c1bbcbb6368b699c699
Source dataset
uspto-grants-1985_01
Patent number
US04493730

Reaction notes

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