Carbamic acid, ethyl ester → Ethyl difluoroacetylcarbamate

HRID 2073682Notes

Reaction equation

HRID 2073682 reaction equation
S(Cl)(Cl)=O.[F:5][CH:6]([F:10])[C:7](O)=[O:8].[NH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[F:5][CH:6]([F:10])[C:7]([NH:11][C:12](=[O:13])[O:14][CH2:15][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 9788Difluoroacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 14392483Ethyl difluoroacetylcarbamateYield 93.3%

Procedure

During a thirty minute period 65.4 g (0.55 mole) of thionyl chloride was added dropwise to 50.0 g (0.52 mole) of difluoroacetic acid with stirring, while maintaining a reaction temperature of 20°-25° C. After complete addition the mixture was stirred at room temperature for 1.5 hours and 46.4 g (0.52 mole) of urethane was added. The resultant mixture was heated at reflux for approximately three hours then allowed to cool to room temperature and stir for approximately 18 hours. The reaction mixture was again heated at 77° C. for two hours. Unreacted materials were removed from the reaction mixture by evaporation under reduced pressure leaving 81.1 g of ethyl difluoroacetylcarbamate as a semi-solid residue.

Workup

  1. temperaturewhile maintaining a reaction temperature of 20°-25° C
  2. additionAfter complete addition the mixture
  3. stirringwas stirred at room temperature for 1.5 hours
  4. temperatureat reflux for approximately three hours
  5. stirringstir for approximately 18 hours
  6. temperatureThe reaction mixture was again heated at 77° C. for two hours
  7. customUnreacted materials were removed from the reaction mixture by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4d3d22dfc2324fdbaed950a723fdcc17
Source dataset
uspto-grants-1990_04
Patent number
US04919708

Reaction notes

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