Water → HCID 15477220, compound

HRID 366328Notes

Reaction equation

HRID 366328 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[C:11]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])=[C:10]([F:25])[CH:9]=[C:8]([Cl:26])[C:6]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33]([SH:35])[CH3:34].O>CN(C)C=O>[Cl:26][C:8]1[C:6]2[CH:7]=[C:3]([CH2:2][S:35][CH2:33][CH3:34])[O:4][C:5]=2[C:11]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[N:14]([CH3:23])[C:13]2=[O:24])=[C:10]([F:25])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 15477212HCID 15477212, compound

Product 1

HCID 15477220HCID 15477220, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (3.3 mmol) of 3-(2-bromomethyl-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.7 g (5.1 mmol) of potassium carbonate were suspended in 20 ml of N,N-dimethylformamide, and 0.21 g (3.4 mmol) of ethylmercaptan was added thereto at room temperature, followed by stirring at room temperature for 1 hour. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 83.4%) of the desired product as a yellowish brown glassy substance. Refractive index: 1.5629 (20° C.).

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-26677ad3d7c7475a9b6477702afdce75
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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