Dimethylformamide → HCID 22120000, compound

HRID 1274654Notes

Reaction equation

HRID 1274654 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]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27].CN(C)C=O.[CH2:33](I)[CH3:34].[H-].[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[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]([CH:21]([CH2:33][CH3:34])[C:22]([O:24][CH3:25])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22119857HCID 22119857, compound

Product 1

HCID 22120000HCID 22120000, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate (0.400 g, 0.00100 mol), N,N-dimethylformamide and ethyl iodide (0.980 g, 0.00628 mol) is added sodium hydride (60%, 0.0900 g, 0.00225 mol) in portions. The mixture is stirred 5 days at room temperature, diluted with methylene chloride, washed sequentially with 8% hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel with ether:hexanes:methylene chloride to give the title compound (0.260 g, 60.9%) which is identified by NMR spectral analysis.

Workup

  1. washwashed sequentially with 8% hydrochloric acid, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-8d1f266d58d0401ea0ca3dd65588f40b
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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