Morpholine → HCID 53857523, compound

HRID 2300681Notes

Reaction equation

HRID 2300681 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CC(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

Product 1

HCID 53857523HCID 53857523, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid (1.43 g), morpholine (2.2 ml) and 2-propanol (20 ml) was stirred under reflux for 4 hours. The reaction mixture was concentrated, and water was added to the residue. The pH was then adjusted 3 with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-morpholino-5-oxazolepropionic acid (1.64 g, 98%). This was recrystallized from ethanol to give colorless needles. mp 180-181° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the residue
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f9a996c9c536451590e09605ab961ceb
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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