Ethyl trichloroacetate → HCID 12292572, compound

HRID 1649326Notes

Reaction equation

HRID 1649326 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].ClC(Cl)(Cl)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>CN(C)C1C=CN=CC=1>[C:9]([N:3]1[CH2:4][CH2:5][O:1][C:2]1=[O:6])([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 10588Ethyl trichloroacetateHCID 739492-Oxazolidinone

Product 1

HCID 12292572HCID 12292572, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 2-oxazolidinone (9.0 g, 0.10 mole) and 25 ml (0.18 mole) of ethyl trichloroacetate were heated to 120° C. in an oil bath. A small amount (ca 50 mg) of 4-dimethylaminopyridine was added to the stirred solution, during which time vigorous reflux began. After removing most of the chloroform by a Dean-Stark trap, the dark solution was allowed to cool to room temperature. Bulb to bulb distillation at 105° C.-120° C. (0.05 mm) yielded 14.1 g (0.0887 mole, 89 percent yield) of the product as a clear liquid which solidified to a colorless solid (mp 40° C.-44° C.) on standing at room temperature. Spectral data confirmed its structure.

Workup

  1. temperaturevigorous reflux
  2. customAfter removing most of the chloroform by a Dean-Stark trap
  3. temperatureto cool to room temperature
  4. distillationBulb to bulb distillation at 105° C.-120° C. (0.05 mm)

Sources & evidence

ORD record
ord-7dcfdac66ef640cf8b58e28e5cb95e79
Source dataset
uspto-grants-1983_11
Patent number
US04416818

Reaction notes

Loading…