Sodium Hydroxide → 5-Methyl-1H-benzo[c][1,2,6]thiadiazin-4-amine-2,2-dioxide

HRID 471492

Reaktionsgleichung

Reaktionsgleichung von HRID 471492
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:10][S:11]([NH2:14])(=[O:13])=[O:12])#[N:2].[OH-].[Na+]>CCO>[CH3:9][C:8]1[C:3]2[C:1]([NH2:2])=[N:14][S:11](=[O:13])(=[O:12])[NH:10][C:4]=2[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67097231N-(2-cyano-3-methylphenyl)sulfamide

Produkt 1

HCID 252228145-Methyl-1H-benzo[c][1,2,6]thiadiazin-4-amine-2,2-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(2-cyano-3-methylphenyl)sulfamide (Example 24a) (211 mg, 1.0 mmol) in EtOH was treated with NaOH (2.0 N, 1.0 mL, 2.0 mmol) and the resultant solution was heated to 100° C. and stirred at that temperature for 0.5 h. After cooling to room temperature, the clear reaction solution was filtered and the filtration was carefully neutralized with 10% AcOH while with vigorous stirring at 0° C. The resultant precipitate was collected by filtration, washed with warm water and 20% EtOH in water to give the title product 5-Methyl-1H-benzo[c][1,2,6]thiadiazin-4-amine-2,2-dioxide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.59 (s, 3H), 6.85-6.87 (d, J=8.4 Hz, 1H), 6.92-6.94 (d, J=7.2 Hz, 1H), 7.24 (s, 1H), 7.37 (t, J=7.6 Hz, 1H), 8.24 (s, 1H), 10.76 (s, 1H). MS 212 (MH+).

Aufarbeitung

  1. filtrationthe clear reaction solution was filtered
  2. filtrationthe filtration
  3. stirringwith vigorous stirring at 0° C
  4. filtrationThe resultant precipitate was collected by filtration
  5. washwashed with warm water and 20% EtOH in water

Quellen und Nachweise

ORD-Eintrag
ord-b9cdb1caa1364f87a4d4e8cae53319a3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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