Sodium Methoxide → HCID 15764727, compound

HRID 326819Notes

Reaction equation

HRID 326819 reaction equation
[CH3:1][S:2][C:3]([C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[CH:4]N(C)C.C(O)(=O)C.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[NH:30])=[CH:27][CH:26]=1.C[O-].[Na+]>CO>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]2[N:31]=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:10]=3)[C:3]([S:2][CH3:1])=[CH:4][N:30]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 54297611HCID 54297611, compoundHCID 67786628HCID 67786628, compound

Product 1

HCID 15764727HCID 15764727, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.8 g of 1-methylmercapto-1-(3-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethene, 2.3 g of 4-chlorobenzamidine acetate and 650 mg of sodium methoxide were added to 200 ml of methanol and the resulting mixture was allowed to react under reflux for 5 hours. After completion of the reaction, the solvent was distilled away under reduced pressure. After adding water, the residue was extracted with ethyl acetate and subjected to column chromatography. Thus 2.5 g of 2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methylmercaptopyrimidine was obtained (Compound 150).

Workup

  1. customto react
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionAfter adding water
  6. extractionthe residue was extracted with ethyl acetate

Sources & evidence

ORD record
ord-6effc4b159164533b12f8aff97aeecfa
Source dataset
uspto-grants-1993_12
Patent number
US05270467

Reaction notes

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