Isobutyl isothiocyanate → HCID 178448905, Verbindung

HRID 1066126

Reaktionsgleichung

Reaktionsgleichung von HRID 1066126
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH2:13]([N:17]=[C:18]=S)[CH:14]([CH3:16])[CH3:15]>C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[S:9](=[O:11])(=[O:10])[N:12]=[C:18]([NH:17][CH2:13][CH:14]([CH3:16])[CH3:15])[NH:1][C:2]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 68960Isobutyl isothiocyanateHCID 777902-Amino-4-chlorobenzenesulphonamide

Produkt 1

HCID 178448905HCID 178448905, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-amino-4-chlorobenzenesulfonamide (5.0 g, 24.18 mmol) and isobutyl isothiocyanate (10 ml, 83.6 mmol) was heated at 150° C. for 3 h. The mixture was allowed to cool and then stirred with 50 ml of ethyl acetate for 30 min. The precipitate was isolated by filtration and recrystallised from ethanol to give 2.9 g (42%) of the pure title compound; m.p. 298-301° C.; 1H-NMR (DMSO-d6): δ 0.91 (d, 6H, CH(CH3)2), 1.83 (m, 1H, CH(CH3)2), 3.05 (t, 2H, CH2), 7.2-7.4 (m, 3H, ArH+NH), 7.67 (d, 1H, ArH), 10.5 (br.s, 1H, NH); MS: m/e 287/289 (M+); (C11H14N3Cl1O2S1) calc. C, 45.91; H, 4.90; N, 14.60; found C, 45.90; H, 5.04; N, 14.66.

Aufarbeitung

  1. temperatureto cool
  2. customThe precipitate was isolated by filtration
  3. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ee324be6274f4edaa8faeee3e26acfe8
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242443B1

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