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

HRID 567167Notes

Reaction equation

HRID 567167 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 2N 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-e586ab153b3c4bc490f3b9cae6ce42f4
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

Loading…