Cyclopentyl isothiocyanate → HCID 178527175, Verbindung

HRID 1066130

Reaktionsgleichung

Reaktionsgleichung von HRID 1066130
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH:13]1([N:18]=[C:19]=S)[CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[CH:13]1([NH:18][C:19]2[NH:1][C:2]3[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=3[S:9](=[O:11])(=[O:10])[N:12]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

4

Edukt 2

HCID 141792Cyclopentyl isothiocyanateHCID 211978072-Amino-4-fluorobenzenesulfonamide

Produkt 1

HCID 178527175HCID 178527175, VerbindungAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2-amino-4-fluorobenzenesulfonamide (1.71 g, 9 mmol) and cyclopentyl isothiocyanate (4.6 ml, 36 mmol) was heated at 140° C. for 4 h. The mixture was cooled to room temperature and stirred with 50 ml of ethyl acetate. The precipitate was isolated by filtration and recrystallised from ethanol to give 591 mg (23%) of the title compound; m.p. 295-298° C.; 1H-NMR (DMSO-d6): δ 1.37-2.02 (m, 8H, cyclopentyl), 4.05 (sext, 1H, CH), 6.97-715 (m, 2H, ArH), 7.32 (br.s, 1H, NH), 7.72 (dd, 1H, ArH), 10.35 (br.s, 1H, NH; MS: m/e 283 (M+, 21%); (C12H14N3F1O2S1) calc. C, 50.87; H, 4.98; N, 14.83; found C, 50.75; H, 5.12; N, 14.93.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe precipitate was isolated by filtration
  3. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-438aab06e804470994859c999b1d24c6
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242443B1

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