Hydrochloric Acid → 6-Bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

HRID 515211Notes

Reaction equation

HRID 515211 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH3:10])[C:5]([NH2:8])=[CH:6][CH:7]=1.[S:11](N)(N)(=[O:13])=[O:12].N1C=CC=CC=1.Cl>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][S:11](=[O:13])(=[O:12])[N:9]([CH3:10])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 82267SulfamideHCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

Product 1

HCID 674127626-Bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

To a round bottom flask was added 4-bromo-N2-methylbenzene-1,2-diamine (1-2) (9.07 g, 45.1 mmol), sulfamide (8.84 g, 92 mmol), and finally anhydrous pyridine (75 mL). The reaction mixture was then heated to 125° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 14 hours. The crude reaction mixture was then allowed to cool to room temperature, suspended in ethyl acetate and added 6N HCl until pH <3. Crude mixture was then filtered. Filtrate organics were separated, then washed with 6N HCl twice dried over sodium sulfate, filtered, and concentrated to give 6-bromo-1-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3). HRMS (M+H)+: observed=262.9486, calculated=262.9484.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe crude reaction mixture
  4. temperatureto cool to room temperature
  5. filtrationCrude mixture was then filtered
  6. customFiltrate organics were separated
  7. washwashed with 6N HCl
  8. dry with materialtwice dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c7c223fec1564661bd299b6f57028ed1
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

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