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

HRID 2396085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396085
[CH3:1][CH:2]([NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH3:3].C(Cl)Cl.[S:13](Cl)[Cl:14]>N1C=CC=CC=1>[Cl:14][S:13][N:4]([CH:2]([CH3:3])[CH3:1])[C:5](=[O:9])[O:6][CH2:7][CH3:8]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 17433Ethyl isopropylcarbamateHCID 25353Sulfur dichloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 mlof 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 dropwiseover 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 pyridine in hydrochloride and evaporation of hexane resulted an orange oil which was distilled in a Kugelrohr apparatus to give 12.5 g of the title Compound B.P.: 64°-80° (bath temp.)

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 pyridine in hydrochloride and evaporation of hexane
  6. customresulted an orange oil which
  7. distillationwas distilled in a Kugelrohr apparatus

Quellen und Nachweise

ORD-Eintrag
ord-002621d69baa40069fe0f4bc1383a5e8
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491162

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