Ethanol → Ethyl 2,2-dimethyl-5-oxo-1-imidazolidineacetate

HRID 256358Notes

Reaction equation

HRID 256358 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1([CH3:16])[NH:10][CH2:9][C:8](=[O:11])[N:7]1[CH2:12][C:13]([O-:15])=[O:14].[Na+].[CH2:18](O)[CH3:19]>>[CH3:5][C:6]1([CH3:16])[NH:10][CH2:9][C:8](=[O:11])[N:7]1[CH2:12][C:13]([O:15][CH2:18][CH3:19])=[O:14]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24386Thionyl ChlorideHCID 23686064Sodium 2,2-dimethyl-5-oxo-1-imidazolidineacetate

Product 1

HCID 53986652Ethyl 2,2-dimethyl-5-oxo-1-imidazolidineacetate

Conditions

Temperature
0 °C

Procedure

(1) To an ice-cold solution of thionyl chloride (5 ml) in dry ethanol (50 ml) a solution of sodium 2,2-dimethyl-5-oxo-1-imidazolidineacetate (4 g) in dry ethanol (50 ml) was added dropwise. The mixture was stirred at 0° C. for 1 hour, then at room temperature overnight. After evaporation under reduced pressure, the residue was taken up with a saturated solution of sodium hydrogen carbonate and extracted with 3×100 ml of dichloromethane. The organic layer was dried and evaporated, to yield ethyl 2,2-dimethyl-5-oxo-1-imidazolidineacetate (2.57 g) as a colorless oil (Rf. 0.49, methanol/acetone 1:1; silica gel plates). Oxalate salt m.p. 109°-113° C. (ethanol/diethyl ether).

Workup

  1. customat room temperature
  2. customovernight
  3. customAfter evaporation under reduced pressure
  4. extractionextracted with 3×100 ml of dichloromethane
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-84e623737adb4623a366e29015fa09fa
Source dataset
uspto-grants-1987_10
Patent number
US04703054

Reaction notes

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