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

HRID 2396079Notes

Reaction equation

HRID 2396079 reaction equation
[CH3:1][CH:2]([NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH3:3].[Cl-].[S:11](Cl)[Cl:12]>N1C=CC=CC=1>[Cl:12][S:11][N:4]([CH:2]([CH3:3])[CH3:1])[C:5](=[O:9])[O:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 312ChlorideHCID 17433Ethyl isopropylcarbamateHCID 25353Sulfur dichloride

Product 1

HCID 20139494Ethyl (chlorosulfenyl)(1-methylethyl)carbamateYield 63.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 mlmethylene chloride cooled to 0° C. was added sulfur dichloride (11.3g, 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 hexaneresulted 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.

Workup

  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
  6. distillationwas distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-e8f9e27215db4393b9936f94e2f452b6
Source dataset
uspto-grants-1996_02
Patent number
US05491162

Reaction notes

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