Dimethyl Sulfate → 3-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 36803

Reaction equation

HRID 36803 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:6][C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]2=[O:25])=[C:4]([F:26])[CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:6][C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[N:16]([CH3:27])[C:15]2=[O:25])=[C:4]([F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 111124793-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 154053043-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 118.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.00 g (2.41 mmol) of 3-(4-chloro-5-ethylsulfonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was dissolved in 10 ml of acetone, and 0.17 g (1.20 mmol) of anhydrous potassium carbonate and 0.23 ml (2.41 mmol) of dimethyl sulfate were added thereto and the reaction was continued for 1.5 hours. After acetone was distilled off, the reaction product was dissolved in ethyl acetate, washed with water and saturated saline solution, and dried over anhydrous sodium sulfate. Thereafter the ethyl acetate was distilled off to obtain a crude product. The crude product was recrystallized from chloroformdiethyl ether, thereby obtaining 0.61 g of the objective product (yield: 59%) in the form of light yellow crystals.

Workup

  1. distillationAfter acetone was distilled off
  2. dissolutionthe reaction product was dissolved in ethyl acetate
  3. washwashed with water and saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter the ethyl acetate was distilled off
  6. customto obtain a crude product
  7. customThe crude product was recrystallized from chloroformdiethyl ether

Sources & evidence

ORD record
ord-30fbf4b7c40d4fae8e27479de6bcd0ff
Source dataset
uspto-grants-1995_05
Patent number
US05416236

Linked notes

Loading…