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

HRID 1259325Notes

Reaction equation

HRID 1259325 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 N-(2-hydroxypropyl)-N′-[3-(trifluoromethyl)-phenyl]ethanediamide (8.80 g, 99%) 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-5afb1ca166a64f41be7c4eb69871f202
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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