Potassium Hydroxide → HCID 86741861, compound

HRID 247037Notes

Reaction equation

HRID 247037 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([S:11][CH3:12])[N:5]=1.Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([C:23]([F:26])([F:25])[F:24])=[C:16]([Cl:27])[C:15]=1[N+:28]([O-:30])=[O:29]>CS(C)=O>[Cl:27][C:16]1[C:15]([N+:28]([O-:30])=[O:29])=[C:14]([N:7]2[C:8]([Cl:10])=[CH:9][C:4]([NH2:3])=[N:5][CH:6]2[S:11][CH3:12])[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]=1[C:23]([F:25])([F:26])[F:24]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 86741861HCID 86741861, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

7.9 parts of finely powdered 85% potassium hydroxide are dissolved in 70 ml of dimethylsulfoxide. To this solution is added dropwise a solution of 17.6 parts of 4-amino-6-chloro-2-methylmercaptopyrimidine in 80 ml of dimethylsulfoxide at about 15° C., and the reaction mixture is subsequently stirred for half an hour at room temperature. Then 30.5 parts of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene in 100 ml of dimethylsulfoxide are added dropwise at about 115° C. The reaction mixture is stirred overnight at room temperature, then poured into 2 liters of ice-water and extracted with ethyl acetate. The combined extracts are washed repeatedly with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by column chromatography over silica gel with dichloromethane as eluant. Yield: 22.3 parts of the title compound with a melting point of 171°-175° C.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography over silica gel with dichloromethane as eluant

Sources & evidence

ORD record
ord-d284fcb7eceb4228854ecc56e5ef09f3
Source dataset
uspto-grants-1987_11
Patent number
US04705790

Reaction notes

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