Acetic Acid → N-(3'-Chloro-2',6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4-chloro-6-methoxypyrimidine

HRID 1904871Notes

Reaction equation

HRID 1904871 reaction equation
[NH2:1][C:2]1[C:3]([Cl:10])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[C:14]([Cl:25])[C:13]=1[N+:26]([O-:28])=[O:27].CC([O-])(C)C.[K+].C(O)(=O)C>CS(C)=O>[Cl:25][C:14]1[C:13]([N+:26]([O-:28])=[O:27])=[C:12]([N:6]2[C:7]([O:8][CH3:9])=[C:2]([NH2:1])[C:3]([Cl:10])=[N:4][CH2:5]2)[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]=1[C:21]([F:23])([F:24])[F:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzeneHCID 8177014-Chloro-6-methoxypyrimidin-5-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 86743151N-(3'-Chloro-2',6'-dinitro-4'-trifluoromethylphenyl)-5-amino-4-chloro-6-methoxypyrimidineYield 103.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

2.84 g (17.8 mmoles) of 5-amino-4-chloro-6-methoxypyrimidine are dissolved in 20 ml of dimethylsulfoxide. With stirring, a solution of 6.24 g (20.5 mmoles) of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene in 15 ml of dimethylsulfoxide and a solution of 2.30 g (20.5 mmoles) of potassium tert-butylate in 15 ml of dimethylsulfoxide are added simultaneously dropwise at 15° C. The dark red solution so obtained is stirred for 1 hour at 15°-20° C. and then poured into ice-water, neutralised with acetic acid and extracted three time with chloroform. The extracts are dried over sodium sulfate and the solvent is removed by rotary evaporation, affording 7.9 g of an oil. This crude product is purified by chromatography through a column of silica gel affording 3.19 g of a crystalline product. Recrystallisation from a mixture of 2 ml of toluene and 8 ml of cyclohexane yields 2.52 g of yellow crystals of m.p. 114°-116° C.

Workup

  1. customThe dark red solution so obtained
  2. stirringis stirred for 1 hour at 15°-20° C.
  3. extractionextracted three time with chloroform
  4. dry with materialThe extracts are dried over sodium sulfate
  5. customthe solvent is removed by rotary evaporation

Sources & evidence

ORD record
ord-10196696d5504ca180dce76c02129524
Source dataset
uspto-grants-1989_06
Patent number
US04840662

Reaction notes

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