Diethyl Oxalate → 4-(3,4,5-Trifluorobenzyl)morpholine-2,3-dione

HRID 1436084

Reaction equation

HRID 1436084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:14])[C:12]=1[F:13])[CH2:5][NH:6]CCO.[C:15]([O:22][CH2:23][CH3:24])(=[O:21])[C:16]([O:18]CC)=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:14])[C:12]=1[F:13])[CH2:5][N:6]1[CH2:24][CH2:23][O:22][C:15](=[O:21])[C:16]1=[O:18]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 63050512HCID 63050512, compound

Product 1

HCID 690103374-(3,4,5-Trifluorobenzyl)morpholine-2,3-dione

Conditions

Temperature
170 °C

Procedure

A mixture of 2-[(3,4,5-trifluorobenzyl)amino]ethanol (6.91 g) and diethyl oxalate (20 mL) was stirred at 170° C. for one hour. The reaction solution was concentrated under reduced pressure, and then a diethyl ether was added to the residue. The precipitated crystals were collected by filtration and then air-dried to obtain 7.38 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiona diethyl ether was added to the residue
  3. filtrationThe precipitated crystals were collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-94e074c546c94546a00db6bf96662b77
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Linked notes

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