Hydrochloric Acid → HCID 20026014, compound

HRID 1722956Notes

Reaction equation

HRID 1722956 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[NH:14][C:13]2=[O:20])=[C:4]([F:21])[CH:3]=1.[H-].[Na+].Cl[CH:25]([F:27])[F:26].Cl>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[N:14]([CH:25]([F:27])[F:26])[C:13]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 24758Sodium hydrideHCID 20025980HCID 20025980, compound

Product 1

HCID 20026014HCID 20026014, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.00 g of 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6 -methyl-2,4(1H,3H)-pyrimidinedione in 20 ml dimethylformamide is added dropwise at room temperature while stirring within 30 minutes to a suspension of 0.28 g of a 55% sodium hydride dispersion in 10 ml of dimethylformamide. The mixture is subsequently stirred for 30 minutes and thereafter 5.26 g of chlorodifluoromethane are introduced at 55° C. while stirring during 18 hours. The reaction mixture is cooled, poured into a solution of 20 ml of 2N hydrochloric acid in 300 ml of water and extracted with 150 ml of ethyl acetate. The organic phase is washed twice with 100 ml of water each time, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is dissolved in 100 ml of diethyl ether and the solution is treated with active carbon and filtered. The filtrate is evaporated to dryness and the residue is recrystallized from diethyl ether/n-hexane. There is obtained 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1-difluoromethyl-6 -methyl-2,4(1H,3H)-pyrimidinedione, m.p. 97°-99° C.

Workup

  1. stirringwhile stirring during 18 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with 150 ml of ethyl acetate
  4. washThe organic phase is washed twice with 100 ml of water each time
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe residue is dissolved in 100 ml of diethyl ether
  8. additionthe solution is treated with active carbon
  9. filtrationfiltered
  10. customThe filtrate is evaporated to dryness
  11. customthe residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-32f0609e9baf4cfaa25d94a366705d58
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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