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

HRID 1614150Notes

Reaction equation

HRID 1614150 reaction equation
[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]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 17433Ethyl isopropylcarbamateHCID 25353Sulfur dichloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

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

Sources & evidence

ORD record
ord-65e79821a2a64cf883fb2de8e5d95798
Source dataset
uspto-grants-1993_03
Patent number
US05196408

Reaction notes

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