Bromine → HCID 22119916, compound

HRID 1274638Notes

Reaction equation

HRID 1274638 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)(=[O:3])[CH3:2].[Br:26]Br>C(OCC)(=O)C.Br>[Br:26][CH2:2][C:1]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)=[O:3]

Participants

5

Reactant 2

HCID 24408BromineHCID 22119925HCID 22119925, compound

Product 1

HCID 22119916HCID 22119916, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of 3-(3-acetyl-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.800 g, 0.00217 mol) in ethyl acetate at room temperature is added hydrobromic acid (48%, 3 drops) followed by bromine in ethyl acetate (0.522 M, 4.35 ml, 0.00277 mol). The resultant mixture is stirred two hours at reflux, cooled to room temperature, diluted with ethyl acetate, washed sequentially with sodium thiosulfate, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a white solid. The solid is recrystallized from hexanes:ethyl acetate to give the title compound as a white, crystalline solid (mp 191-193° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. washwashed sequentially with sodium thiosulfate, saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid
  6. customThe solid is recrystallized from hexanes

Sources & evidence

ORD record
ord-cf4bf1ff1a2d40a1be3fb140044d4167
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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