Methyl iodide → Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

HRID 48997Notes

Reaction equation

HRID 48997 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4](=[O:12])[N:3]1[C:13]1[CH:14]=[CH:15][C:16]2[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH:27]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C)C=O.O>[CH3:28][N:7]1[C:6]([C:8]([F:9])([F:10])[F:11])=[CH:5][C:4](=[O:12])[N:3]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=3[CH:27]=2)[C:2]1=[O:1]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10960337Ethyl 5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

Product 1

HCID 11729347Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetateYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-[3,6-dihydro-2,6-dioxo-4-(tri-fluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate (0.643 g, 0.00160 mol) and potassium carbonate (0.243 g, 0.00170 mol) in N,N-dimethylformamide is stirred at room temperature for 90 minutes, treated with iodomethane (0.320 mL, 0.00500 mol), stirred at room temperature overnight, and diluted with water. The resultant aqueous mixture is extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and a 10% ethyl acetate in hexanes solution gives the title product as a tan solid (0.362 g, mp 150-152° C.).

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe resultant aqueous mixture is extracted with methylene chloride
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a brown oil

Sources & evidence

ORD record
ord-20ba00d016c74c03b67f42b5bcd07b76
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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