4-(Trifluoromethyl)aniline → Valine, N-[4-(trifluoromethyl)phenyl]-

HRID 1389352Notes

Reaction equation

HRID 1389352 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Br[CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].CN(P(N(C)C)(N(C)C)=O)C>O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C@H:13]([C:14]([OH:16])=[O:15])[CH:17]([CH3:19])[CH3:18])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 99644-(Trifluoromethyl)anilineHCID 112682-Bromoisovaleric acidHCID 11430Potassium Carbonate2×HCID 12679Hexamethylphosphoramide

Product 1

HCID 13388454Valine, N-[4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of p-trifluoromethylaniline, 2.25 g of α-bromoisovaleric acid and 2.0 g of potassium carbonate is heated at 100° for 1 hour. After 1.5 hour, 5 ml of HMPT is added and the mixture heated at 100° for 15 hr. The mixture is then poured into water and potassium carbonate added to about pH 11. The mixture is washed with ether, methylene chloride and the aqueous phase acidified to about pH 3 and washed with ether and concentrated. The residue is recrystallized from hexane/ether to yield N-(4-trifluoromethylphenyl)valine, which is reacted with m-phenoxybenzyl bromide to yield the m-phenoxybenzyl ester of N-(4-trifluoromethylphenyl)valine. MS m/e 443 (M+, 5.9).

Workup

  1. temperatureis heated at 100° for 1 hour
  2. temperaturethe mixture heated at 100° for 15 hr
  3. additionadded to about pH 11
  4. washThe mixture is washed with ether, methylene chloride
  5. washwashed with ether
  6. concentrationconcentrated
  7. customThe residue is recrystallized from hexane/ether

Sources & evidence

ORD record
ord-360c1d1dda804dfc933640ea040eb795
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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