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

HRID 1772669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772669
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

Komponenten

5

Edukt 2

HCID 82267SulfamideHCID 12198271HCID 12198271, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a73773738bc140518fb058ea10f4d9b8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249163B2

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