Hydrochloric Acid → 4-(4-Chlorophenyl)-2-isopropoxy-5-oxazolepropionic acid

HRID 2300675Notes

Reaction equation

HRID 2300675 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].Cl[C:8]1[O:9][C:10]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:12]=1.Cl>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:12]=[C:8]([O:6][CH:4]([CH3:5])[CH3:3])[O:9][C:10]=2[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

Product 1

HCID 545689074-(4-Chlorophenyl)-2-isopropoxy-5-oxazolepropionic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.60 g) was added to 2-propanol (20 ml), and stirred at room temperature for 10 minutes. To the reaction mixture was added 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid (1.43 g), and stirred under reflux for 30 minutes. Next, water was added to the resulting reaction mixture, which was then acidified with 2 N hydrochloric acid, and the crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-isopropoxy-5-oxazolepropionic acid (1.35 g, 87%). This was recrystallized from isopropyl ether to give colorless prisms. mp 116-117° C.

Workup

  1. stirringstirred
  2. temperatureunder reflux for 30 minutes
  3. customthe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2899ac922509441dacef1786430d2d3c
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

Loading…