Water → Sodium 3-Benzoyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-trifluoromethylbenzofuran-4-carboxylate

HRID 52000Notes

Reaction equation

HRID 52000 reaction equation
[H-].[Na+:2].[C:3]([C:11]1[C:15]2=[C:16]([C:21]([OH:23])=[O:22])[C:17]([OH:20])=[CH:18][CH:19]=[C:14]2[O:13][C:12]=1[C:24]([F:27])([F:26])[F:25])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[N:33]=[C:32](S(C)(=O)=O)[N:31]=1.O>CN(C)C=O>[C:3]([C:11]1[C:15]2=[C:16]([C:21]([O-:23])=[O:22])[C:17]([O:20][C:32]3[N:33]=[C:34]([O:36][CH3:37])[CH:35]=[C:30]([O:29][CH3:28])[N:31]=3)=[CH:18][CH:19]=[C:14]2[O:13][C:12]=1[C:24]([F:27])([F:25])[F:26])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Na+:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 190772713-Benzoyl-5-hydroxy-2-trifluoromethylbenzofuran-4-carboxylic acid

Product 1

HCID 23681721Sodium 3-Benzoyl-5-(4,6-dimethoxypyrimidin-2-yl)oxy-2-trifluoromethylbenzofuran-4-carboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

While stirring 0.35 g of sodium hydride in 30 ml of N,N-dimethylformamide at room temperature, 1.73 g of 3-benzoyl-5-hydroxy-2-trifluoromethylbenzofuran-4-carboxylic acid was gradually added thereto. After completion of the addition, the mixture was further stirred for one hour. While stirring this mixture at room temperature, 1.08 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added thereto, and then the mixture was stirred at 70° C. for 3 hours. The mixture was returned to room temperature and poured into water. Precipitated crystals were separated by filtration and washed with water and acetone to obtain 1.02 g (yield: 40.5%) of the desired compound.

Workup

  1. additionAfter completion of the addition
  2. stirringWhile stirring this mixture at room temperature
  3. stirringthe mixture was stirred at 70° C. for 3 hours
  4. customwas returned to room temperature
  5. customPrecipitated crystals
  6. customwere separated by filtration
  7. washwashed with water and acetone

Sources & evidence

ORD record
ord-a516fc01f4ed45c7a2381437f5b9547c
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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