Water → HCID 136096283, compound

HRID 1461732Notes

Reaction equation

HRID 1461732 reaction equation
[F:1][C:2]([F:14])([C:7]1[N:8]=[CH:9][NH:10][C:11](=[O:13])[CH:12]=1)[C:3]([F:6])([F:5])[F:4].[Cl:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:15][C:12]1[C:11](=[O:13])[NH:10][CH:9]=[N:8][C:7]=1[C:2]([F:1])([F:14])[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 135550576HCID 135550576, compound

Product 1

HCID 136096283HCID 136096283, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-pentafluoroethylpyrimidin-6-one (0.4 g) and N-chlorosuccinimide (0.27 g) in dry dimethylformamide (5 ml) was heated to 80° C. for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water, and extracted into ethyl acetate. The organic layer was dried, over anhydrous magnesium sulphate, filtered, and evaporation of the solvent under reduced pressure gave a brown oil. Recrystallisation from water gave 5-chloro-4-pentafluoroethylpyrimidin-6-one

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe organic layer was dried, over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporation of the solvent under reduced pressure
  5. customgave a brown oil
  6. customRecrystallisation from water

Sources & evidence

ORD record
ord-26fdd47b4fc249998d2d50ebfe457247
Source dataset
uspto-grants-1991_12
Patent number
US05077297

Reaction notes

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