Methyl iodide → 3-(3-chloro-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 48982Notes

Reaction equation

HRID 48982 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]3=[O:22])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.O>[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[N:13]([CH3:23])[C:12]3=[O:22])[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 159065603-(3-chloro-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 159065613-(3-chloro-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-chloro-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.06 g), potassium carbonate (0.470 g) and iodomethane (0.500 mL) in N,N-dimethylformamide is stirred at room temperature for 90 minutes, treated with additional iodomethane (0.500 mL), stirred at room temperature for 15 minutes, and diluted with water. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and dried in a vacuum oven at room temperature to give the title product as a solid which is identified by NMR spectral analysis.

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. washThe solid is washed with water
  5. customdried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-cb86bafad2944ac6b6770e5ace7f0302
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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