Sulfamide → 5-bromo-3-methyl-3,4-dihydro-1H-benzo[1,2,6]thiadiazine 2,2-dioxide

HRID 459794Notes

Reaction equation

HRID 459794 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][NH:10][CH3:11])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[S:12](N)(N)(=[O:14])=[O:13]>N1C=CC=CC=1>[Br:1][C:2]1[C:3]2[CH2:9][N:10]([CH3:11])[S:12](=[O:14])(=[O:13])[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 184444723-Bromo-2-methylaminomethyl-phenylamine

Product 1

HCID 588241275-bromo-3-methyl-3,4-dihydro-1H-benzo[1,2,6]thiadiazine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromo-2-methylaminomethyl-phenylamine from step 3 of Example 3 (2.615 g, 12.2 mmol) in pyridine (50 ml) was added sulfamide (3.5 g, 36.4 mmol). The solution was heated under reflux overnight, and the cooled reaction mixture was partitioned between 2N HCl water solution and ethyl acetate. The organic layer was washed with 2N HCl solution, water, brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 5-bromo-3-methyl-3,4-dihydro-1H-benzo[1,2,6]thiadiazine 2,2-dioxide as a white solid. (2.32 g, 69%) MS: (M+H)+277.1.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux overnight
  3. customthe cooled reaction mixture
  4. customwas partitioned between 2N HCl water solution and ethyl acetate
  5. washThe organic layer was washed with 2N HCl solution, water, brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting brown residue
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-b85f84d2dd6d420db009c3e6e24567fc
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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