Benzoic Acid → Oxiracetam

HRID 2291691Notes

Reaction equation

HRID 2291691 reaction equation
CC(C)C[N:4]1[CH2:8][C:7](=[O:9])[NH:6]C1C(C)C.[OH:14][CH:15]([CH3:20])[CH2:16][C:17]([O-:19])=O.C(O)(=O)C1C=CC=CC=1.O>C(O)CCCC>[OH:14][CH:15]1[CH2:20][N:4]([CH2:8][C:7]([NH2:6])=[O:9])[C:17](=[O:19])[CH2:16]1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 962WaterHCID 86742672HCID 86742672, compound

Product 1

HCID 4626OxiracetamYield 62.1%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A solution of 2-methylpropyl 2-(1-methylethyl)-4-oxoimidazolidine-β-hydroxybutanoate (15 g, 52.4 mmol), benzoic acid (6.4 g, 52.4 mmol) and water (3.75 ml, 208 mmol) in n-pentanol (90 ml) was refluxed under nitrogen for 6 hr. After cooling the mixture was extracted twice with water (35 ml). The aqueous extracts were evaporated to dryness and the residue was crystallized from methanol to give 5.15 g (62.1%) of the title compound, m.p. 167°-70° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionwas extracted twice with water (35 ml)
  3. customThe aqueous extracts were evaporated to dryness
  4. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-22a3f3b71e9c4c9b980f9833c95dc063
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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