N-bromobutanimide → alpha-Bromo-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidyl]-1,2-benzisothiazole-3-acetonitrile

HRID 1274632Notes

Reaction equation

HRID 1274632 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]#[N:23])[C:17]=3[CH:24]=2)[C:3]1=[O:25].[Br:26]N1C(=O)CCC1=O>ClCCCl>[Br:26][CH:21]([C:18]1[C:17]2[CH:24]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:10])([F:11])[F:9])[N:2]([CH3:1])[C:3]3=[O:25])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1)[C:22]#[N:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 221199235-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetonitrile

Product 1

HCID 22119926alpha-Bromo-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidyl]-1,2-benzisothiazole-3-acetonitrileYield 56.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetonitrile (0.500 g, 0.00140 mol) in 1,2-dichloroethane is added N-bromosuccinimide (0.250 g, 0.00140 mol). The resultant mixture is irradiated with a UV lamp and stirred at reflux six hours. Additional N-bromosuccinimide (0.250 g, 0.00140 mol) is added and the resultant mixture is stirred 1.5 hours at reflux under a UV lamp. The mixture is cooled to room temperature and concentrated in vacuo. The resultant residue is taken up in methylene chloride, washed with water, treated with charcoal, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give the title product as a red glass (0.350 g, 56.2%, mp 185-187° C.) which is identified by IR and NMR spectral analyses.

Workup

  1. temperatureat reflux six hours
  2. temperatureat reflux under a UV lamp
  3. concentrationconcentrated in vacuo
  4. washwashed with water
  5. additiontreated with charcoal
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2683a4a7b8a4fb0b62bfa706b4d868d
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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