Bromine → HCID 22119961, compound

HRID 1274653Notes

Reaction equation

HRID 1274653 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:15]3[CH:16]=[C:17]([N:20]4[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]4=[O:32])[CH:18]=[CH:19][C:14]=3[S:13][N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:33]Br>C(OCC)(=O)C.Br>[Br:33][CH:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:8])=[O:9])[C:11]1[C:15]2[CH:16]=[C:17]([N:20]3[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[N:22]([CH3:31])[C:21]3=[O:32])[CH:18]=[CH:19][C:14]=2[S:13][N:12]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 22119993HCID 22119993, compound

Product 1

HCID 22119961HCID 22119961, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 8857Ethyl AcetateSolvent4×

Procedure

To a solution of 3-[3-(phenylsulfonyl)methyl-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.400 g, 0.000831 mol) in ethyl acetate is added 48% hydrobromic acid (4 drops) followed by bromine in ethyl acetate (0.522 M, 1.67 ml, 0.000872 mol). The resultant mixture is stirred 1.5 hours at reflux. Additional bromine in ethyl acetate (1.67 ml) is added and the resultant mixture is stirred one hour at reflux. The mixture is cooled to room temperature, diluted with ethyl acetate, washed sequentially with 0.1 M sodium sulfite, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel with hexanes:ethyl acetate to give the title compound as a white crystalline solid (0.420 g, 90.1%, mp 182-183° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. washwashed sequentially with 0.1 M sodium sulfite, saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel with hexanes

Sources & evidence

ORD record
ord-53c364adc3cf4c958afcd7f0d78fe7a8
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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