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

HRID 1772669Notes

Reaction equation

HRID 1772669 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:9]=[C:8]([NH:10][CH3:11])[C:7]([NH2:12])=[CH:6][CH:5]=1.[S:13](N)(N)(=[O:15])=[O:14]>N1C=CC=CC=1.C(Cl)Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:12][S:13](=[O:15])(=[O:14])[N:10]([CH3:11])[C:8]=2[CH:9]=1

Participants

5

Reactant 2

HCID 82267SulfamideHCID 12198271HCID 12198271, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-N1-methylbenzene-1,2-diamine dihydrochloride (800.0 mg, 3.00 mmol) and sulfamide (560 mg, 5.80 mmol) in pyridine (10 mL) was heated at reflux for 2 h. Pyridine was removed under reduced pressure and the residue obtained was dissolved in DCM (20 mL) and washed with 1N HCl (20 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated to obtain 6-bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.98 (d, J=2.0 Hz, 1H), 7.93 (dd, J=8.8, 2.3 Hz, 1H), 7.46 (d, 1H), 3.41 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customPyridine was removed under reduced pressure
  4. customthe residue obtained
  5. washwashed with 1N HCl (20 mL)
  6. customThe DCM layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a73773738bc140518fb058ea10f4d9b8
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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