Syringaldehyde → 5-[(3,5-Dimethoxy-4-hydroxyphenyl)methylene]-2,4-imidazolidinedione

HRID 128736

Reaction equation

HRID 128736 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[NH:14]1[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[O:16]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:20]2[NH:14][C:15](=[O:16])[NH:17][C:18]2=[O:19])[CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11]

Participants

3

Reactant 2

HCID 8655SyringaldehydeHCID 10006Hydantoin

Product 1

HCID 40887335-[(3,5-Dimethoxy-4-hydroxyphenyl)methylene]-2,4-imidazolidinedioneYield 75.7%

Procedure

Prepared according to the procedure described in Example 90 using 3,5-dimethoxy-4-hydroxybenzaldehyde (5.6 g, 30 mmoles), hydantoin (3.0 g, 30 mmoles), and μ-alanine (1.4 g, 16 mmoles), to afford the pure product (6.0 g), mp 296°-297° C.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ce2b36cfed394d5b93f12afce8243500
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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