Hydrochloric Acid → N-Cyclohexyl-3-sulfanylpropanamide

HRID 1608000

Reaktionsgleichung

Reaktionsgleichung von HRID 1608000
[CH:1]1([NH:7][C:8](=[O:11])[CH:9]=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.NC(N)=[S:15].[OH-].[Na+]>O>[CH:1]1([NH:7][C:8](=[O:11])[CH2:9][CH2:10][SH:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 137811Acrylamide, N-cyclohexyl-HCID 2723790Thiourea

Produkt 1

HCID 14618019N-Cyclohexyl-3-sulfanylpropanamideAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of N-cyclohexylacrylamide (15.3 g), concentrated hydrochloric acid (19.4 g, 37.6%), thiourea (7.6 g) and water (10 g) was heated to 60° C. for 2 hours, cooled to 20° C. and sodium hydroxide (50%, 16 g) was slowly added under nitrogen keeping the temperature below 30° C. The resulting mixture was heated to 60° C. for 1 hour and extracted with methylene chloride (2×50 ml). Removal of the solvent afforded N-cyclohexyl-3-mercaptopropionamide (16.9 g) which was purified by vacuum distillation at 0.05 mm and 130° C. to yield 13.7 g of N-cyclohexyl-3-mercaptopropionamide; m.p. 73.5°-75.5° C.

Aufarbeitung

  1. temperaturecooled to 20° C.
  2. temperatureThe resulting mixture was heated to 60° C. for 1 hour
  3. extractionextracted with methylene chloride (2×50 ml)
  4. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-53ae26dce11243889025a43cfbcb42ac
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04868310

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