Hydrogen Bromide → HCID 178456957, compound

HRID 1066111Notes

Reaction equation

HRID 1066111 reaction equation
[CH:1]([NH:4][C:5]1[NH:10][C:9]2[CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[CH:14][C:8]=2[S:7](=[O:20])(=[O:19])[N:6]=1)([CH3:3])[CH3:2].[BrH:21].OO>O>[Br:21][C:13]1[C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][C:9]2[NH:10][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][S:7](=[O:19])(=[O:20])[C:8]=2[CH:14]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 178456966HCID 178456966, compound

Product 1

HCID 178456957HCID 178456957, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-isopropylamino-6-trifluoromethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (307 mg; 1 mmol) in water (5 ml) was added 40% hydrobromic acid (0.44 ml; 3 mmol). The solution was then heated to 70° C. and 30% hydrogen peroxide (0.33 g; 3 mmol) was added. After 30 min the reaction mixture was cooled and extracted with ethyl acetate (20 ml) and purified by column chromatograpy (ethyl acetate:ethanol 9:1). Concentration of the appropiate fractions produced the title compound (22 mg); 1H-NMR (DMSO-d6) ppm; 7.60 (s, 1H), 7.10 (s, 1H), 6.65 (s, 1H), 3.95 (m, 1H) 1.11 (d, 6H).

Workup

  1. temperatureAfter 30 min the reaction mixture was cooled
  2. extractionextracted with ethyl acetate (20 ml)
  3. custompurified by column chromatograpy (ethyl acetate:ethanol 9:1)

Sources & evidence

ORD record
ord-940b26e893284166b8463ad95488a10a
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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