Pyridine → Ethyl (chlorosulfenyl)(1-methylethyl)carbamate

HRID 232723

Reaktionsgleichung

Reaktionsgleichung von HRID 232723
[CH3:1][CH:2]([NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH3:3].[S:10](Cl)[Cl:11].N1C=CC=CC=1>C(Cl)Cl>[Cl:11][S:10][N:4]([CH:2]([CH3:3])[CH3:1])[C:5](=[O:9])[O:6][CH2:7][CH3:8]

Komponenten

5

Edukt 3

HCID 1049Pyridine2×HCID 17433Ethyl isopropylcarbamateHCID 25353Sulfur dichloride

Produkt 1

HCID 20139494Ethyl (chlorosulfenyl)(1-methylethyl)carbamateAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 ml methylene chloride cooled to 0° C. was added sulfur dichloride (11.3 g, 0.11 mol) in one portion. While maintaining the temperature of the mixture at 0° C., pyridine (8.7 g, 0.11 mol) was added dropwise over eleven minutes. After complete addition of the pyridine the temperature was allowed to rise to room temperature and stirring was continued for additional 1.5 hours. The mixture was let stand overnight. Methylene chloride was evaporated under vacuum and 100 ml hexane was added. Filteration of the pyridine hydrochloride and evaporation of hexane resulted in an orange oil which was distilled in a Kugelrohr apparatus to give 12.5 g of the title compound Bp: 64°-80° (bath temperature) at 1.4 mm Hg.

Aufarbeitung

  1. customto rise to room temperature
  2. waitThe mixture was let stand overnight
  3. customMethylene chloride was evaporated under vacuum and 100 ml hexane
  4. additionwas added
  5. customFilteration of the pyridine hydrochloride and evaporation of hexane
  6. customresulted in an orange oil which
  7. distillationwas distilled in a Kugelrohr apparatus

Quellen und Nachweise

ORD-Eintrag
ord-2a23b4242a5f4f5f9d5abfbbd60b95d4
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591764

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