Dimethyl Sulfate → HCID 22119918, compound

HRID 1274643

Reaction equation

HRID 1274643 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[O:22])[C:17]=3[CH:28]=2)[C:3]1=[O:29].S(OC)(O[CH3:34])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([N:23]([CH3:34])[S:24]([CH3:27])(=[O:26])=[O:25])=[O:22])[C:17]=3[CH:28]=2)[C:3]1=[O:29]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 221199975-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-(methylsulfonyl)-1,2-benzisothiazole-3-carboxamide

Product 1

HCID 22119918HCID 22119918, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-(methylsulfonyl)-1,2-benzisothiazole-3-carboxamide (0.300 g, 0.000670 mol) in acetone is added dimethyl sulfate (0.180 g, 0.00140 mol) followed by potassium carbonate (0.250 g, 0.00180 mol). The resultant mixture is stirred one hour at reflux and concentrated in vacuo. The residue is partitioned between methylene chloride and water. The organic layer is saved and the aqueous layer is extracted with methylene chloride. The combined organic layers are washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel with ethyl acetate:hexanes to give the title compound as a white solid (0.232 g, 74.9%, mp 120-122° C.).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between methylene chloride and water
  4. extractionthe aqueous layer is extracted with methylene chloride
  5. washThe combined organic layers are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-8477a90d3cd24a71922f71a08846ad91
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Linked notes

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