Sodium Hydroxide → HCID 68801647, Verbindung

HRID 1467184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467184
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].N[C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH:16]([CH3:18])[CH3:17])[C:8]=1[C:9]#[N:10].[OH-].[Na+]>CCO>[CH:16]([NH:15][C:11]1[C:8]2[C:9]([NH2:10])=[N:5][S:1](=[O:3])(=[O:2])[NH:4][C:7]=2[CH:14]=[CH:13][CH:12]=1)([CH3:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66747382HCID 66747382, Verbindung

Produkt 1

HCID 68801647HCID 68801647, VerbindungAusbeute 14,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-6-(isopropylamino)benzonitrile sulfamide (Example 157a) (0.14 g, 0.54 mmol) and NaOH (2 N, 0.54 mL) in EtOH (3 mL) was stirred at 90° C. under nitrogen for 0.5 hour. The reaction mixture was cooled to room temperature, and concentrated under vacuum. H2O (1 mL) was added and the reaction mixture was neutralized to pH˜3 with 10% AcOH. The resultant precipitate was extracted with EtOAc, and after evaporation of solvents the residue was purified by preparative thin layer chromatography using a DCM/EtOAc (4:1) solution as eluant, to give N5-isopropyl-1H-benzo[c][1,2,6]thiadiazine-4,5-diamine-2,2-dioxide (0.02 g). 1H NMR (400 MHz, DMSO-d6) δ 1.11 (d, J=6.4 Hz, 6H), 1.84 (bs, 1H), 5.24 (bs, NH), 6.22-6.19 (m, 2H, NH), 7.09 (t, J=8.0 Hz, 1H), 7.48 (bs, 2H). MS 255 (MH+).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionH2O (1 mL) was added
  3. extractionThe resultant precipitate was extracted with EtOAc
  4. customafter evaporation of solvents the residue
  5. customwas purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-754e9343a45e49618c717019e4479289
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000054B2

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