Acetic Acid → HCID 291123, compound

HRID 1464645Notes

Reaction equation

HRID 1464645 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[NH:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].NCCC(O)=O.C(O)(=O)C>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:18]2[NH:12][C:13](=[O:14])[NH:15][C:16]2=[O:17])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 1183VanillinHCID 10006Hydantoin

Product 1

HCID 291123HCID 291123, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzaldehyde (4.6 g, 30 mmoles), hydantoin (3.0 g, 30 mmoles), β-alanine (1.4 g, 16 mmoles), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 4 hours the mixture is stirred into water (350 ml) and the precipitate is filtered off, rinsed successively with water (3×), ethanol (2×), and ether (2×), and dried. Recrystallization from methanol afforded the pure product (3.0 g), mp 272°-273° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed successively with water (3×), ethanol (2×), and ether (2×)
  4. customdried
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e2afb2f181f74c5ea5d9e5d478550f31
Source dataset
uspto-grants-1994_04
Patent number
US05306822

Reaction notes

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