Dimethyl Sulfate → HCID 11013644, compound

HRID 580781Notes

Reaction equation

HRID 580781 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:3]=1[NH:4][N:5]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[NH:7][C:6]1=[O:16].[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:3]=1[NH:4][N:5]1[C:10](=[O:11])[CH:9]=[C:8]([C:12]([F:13])([F:15])[F:14])[N:7]([CH3:22])[C:6]1=[O:16]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 11099869HCID 11099869, compound

Product 1

HCID 11013644HCID 11013644, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

52.5 g (0.154 mol) of 3-(2,3-dichloroanilino)-6-trifluoromethyluracil and 42.67 g (0.309 mol) of potassium carbonate are introduced into 700 ml of acetone. 27.74 g (0.22 mol) of dimethyl sulfate are added, with stirring, at room temperature. The mixture is subsequently refluxed for one hour. After cooling, the solids are filtered off with suction, and the filtrate is concentrated in vacuo. The pale brown crystalline residue is stirred with 500 ml of diisopropyl ether and filtered off with suction. This gives 49.5 g (91% of theory) of 3-(2,3-dichloroanilino)-1-methyl-6-trifluoromethyluracil with a melting point of 179° C. and a retention value of 0.49 (silica gel, hexane/ethyl acetate 1:1).

Workup

  1. temperatureThe mixture is subsequently refluxed for one hour
  2. temperatureAfter cooling
  3. filtrationthe solids are filtered off with suction
  4. concentrationthe filtrate is concentrated in vacuo
  5. stirringThe pale brown crystalline residue is stirred with 500 ml of diisopropyl ether
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-12d09b474e0c4bc7977aafc175f5e6e3
Source dataset
uspto-grants-1999_07
Patent number
US05919732

Reaction notes

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