2-Aminobenzonitrile → 4-amino-1H-2lambda6,1,3-benzothiadiazine-2,2-dione

HRID 2076975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076975
[C:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1N)#[N:2].[S:10]([NH2:14])([NH2:13])(=[O:12])=[O:11].C1CCN2C(=NCCC2)CC1>O>[NH:13]1[C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:1]([NH2:2])=[N:14][S:10]1(=[O:12])=[O:11]

Komponenten

5

Edukt 3

HCID 729132-AminobenzonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82267Sulfamide

Produkt 1

HCID 133303354-amino-1H-2lambda6,1,3-benzothiadiazine-2,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A stirred mixture of 2-cyanoaniline (236 mg, 2.0 mmol), sulfamide (192 mg, 2.0 mmol) and DBU (304 mg, 2.0 mmol) was heated at 160° C. under nitrogen for 3 days. After cooling to room temperature, the reaction mixture was diluted with water and extracted three times with EtOAc. The aqueous layer was removed under vacuum and the residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane to give the title compound as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.03 (dd, J=0.8, 8.0 Hz, 1H), 7.12 (dt, J=0.8, 8.0 Hz, 1H), 7.56 (dt, J=0.8, 8.0 Hz, 1H), 7.85 (dd, J=0.8, 8.0 Hz, 1H). MS 198 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with EtOAc
  3. customThe aqueous layer was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel eluting with 10% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-df01d0b740294492a94af63f6d1a3f66
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928111B2

Notizen zur Reaktion

Wird geladen…