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

HRID 1389339Notes

Reaction equation

HRID 1389339 reaction equation
Br[CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.[OH-].[Na+].CO.[F:37][C:38]([F:47])([F:46])[C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1.[OH-].[Na+]>CO.CN(C)C=O>[F:37][C:38]([F:46])([F:47])[C:39]1[CH:40]=[CH:41][C:42]([NH:43][C@H:2]([C:3]([OH:5])=[O:4])[CH:6]([CH3:8])[CH3:7])=[CH:44][CH:45]=1

Participants

8

Reactant 5

HCID 4764PhenolphthaleinHCID 99644-(Trifluoromethyl)anilineHCID 112682-Bromoisovaleric acidHCID 14798Sodium HydroxideHCID 23721981Sodium hydroxide methanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Two grams of α-bromoisovaleric acid (0.001 mole) dissolved in 10 ml of methanol is titrated to the phenolphthalein end point at 0° with 2 N sodium hydroxide/methanol. The alcohol is then removed and 10 ml of dimethylformamide and p-trifluoromethylaniline (3.54 g, 0.022 mole) added. The reaction mixture is heated at 100° for 2 hours and left at room temperature about 18 hours. The reaction mixture is poured into 50 ml of 0.1 N sodium hydroxide, washed with ether and the aqueous phase adjusted to pH 4 with conc. HCl and then extracted with chloroform (3X). The extracts are combined and washed with brine, dried, concentrated in a rotoevaporator and solvent removed under vacuum at about 50° to yield N-(p-trifluoromethylphenyl)valine.

Workup

  1. customThe alcohol is then removed
  2. temperatureThe reaction mixture is heated at 100° for 2 hours
  3. washwashed with ether
  4. extractionextracted with chloroform (3X)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in a rotoevaporator and solvent
  8. customremoved under vacuum at about 50°

Sources & evidence

ORD record
ord-97586e293797407f90e8a92aed3bd97b
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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