Sulfamide → N-(2-cyano-3-methylphenyl)sulfamide

HRID 711631

Reaktionsgleichung

Reaktionsgleichung von HRID 711631
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[S:11](N)([NH2:14])(=[O:13])=[O:12]>O1CCOCC1>[C:4]([C:3]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][S:11]([NH2:14])(=[O:13])=[O:12])#[N:5]

Komponenten

4

Edukt 2

HCID 82267SulfamideHCID 2799732-Amino-6-methylbenzonitrile

Produkt 1

HCID 67097231N-(2-cyano-3-methylphenyl)sulfamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-amino-6-methylbenzonitrile (1.32 g, 10 mmol) and sulfamide (4.81 g, 50 mmol) in dry 1,4-dioxane (50 mL) was refluxed under nitrogen for 3 days. After the reaction mixture was cooled down to room temperature, the precipitate was filtered and washed with dioxane. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel eluting with EtOAc/hexanes (3:7) to give the title compound as a pale-white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.44 (s, 3H), 7.19-7.21 (m, 3H), 7.39-7.41 (d, J=8.4 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 9.41 (s, 1H).

Aufarbeitung

  1. filtrationthe precipitate was filtered
  2. washwashed with dioxane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel eluting with EtOAc/hexanes (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-347f0b4d6d274ab5a4efd9b6d82d3170
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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