1-Amino-2-propanol → N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamide

HRID 1958304Notes

Reaction equation

HRID 1958304 reaction equation
[O:1]=[C:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[C:3]([O:5]CC)=O.[NH2:19][CH2:20][CH:21]([OH:23])[CH3:22]>C(O)C>[OH:23][CH:21]([CH3:22])[CH2:20][NH:19][C:3](=[O:5])[C:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)=[O:1]

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 1805242ethyl 2-oxo-2-[3-(trifluoromethyl)anilino]acetate

Product 1

HCID 2917089N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl oxo{[3-(trifluoromethyl)-phenyl]amino}acetate (8.04 g, 30.7 mmol) was dissolved in ethanol (50 ml, 99.5%). To the stirred solution was added 1-amino-2-propanol (racemic, 2.32 g, 31 mmol) in one portion, and the mixture was heated to reflux for 90 minutes. The mixture was allowed to cool and was evaporated to dryness, giving 8.80 g (99%) of N-(2-hydroxypropyl)-N′-[3-(trifluoromethyl)-phenyl]ethanediamide as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 90 minutes
  3. temperatureto cool
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-f00096d184ea48c1b562b56becea8a61
Source dataset
uspto-grants-2013_04
Patent number
US08410114B2

Reaction notes

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