Sodium Methoxide → 2-(2,4-Difluorophenyl)-4-(3-trifluoromethylphenyl)-5-meth anesulfonylpyrimidine

HRID 326817Notes

Reaction equation

HRID 326817 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9]N(C)C)=O.Cl.[F:23][C:24]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:25]=1[C:26]([NH2:28])=[NH:27].C[O-].[Na+]>CO>[F:23][C:24]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:25]=1[C:26]1[N:28]=[C:6]([C:5]2[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=2)[C:8]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:9][N:27]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 200809312,4-Difluoro-benzamidine hydrochlorideHCID 541640061-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene

Product 1

HCID 150368532-(2,4-Difluorophenyl)-4-(3-trifluoromethylphenyl)-5-meth anesulfonylpyrimidineYield 77.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g of 1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene and 4.6 g of 2,4-difluorobenzamidine hydrochloride were dissolved in 30 ml of methanol at room temperature and 1.2 g of sodium methoxide was added thereto. The resulting mixture was heated under reflux for an hour. The solvent was distilled away under reduced pressure. The residue was washed with water and then dried to obtain 6 g of 2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine (Compound 147).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for an hour
  3. distillationThe solvent was distilled away under reduced pressure
  4. washThe residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-bf22a960eacf49cfb48a84eb6a4b1394
Source dataset
uspto-grants-1993_12
Patent number
US05270467

Reaction notes

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