Syringaldehyde → 5-[(3,5-Dimethoxy-4-hydroxyphenyl)methylene]-1-methyl-2,4-imidazolidinedione

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.[CH3:14][N:15]1[CH2:21][C:19](=[O:20])[NH:18][C:16]1=[O:17]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:21]2[N:15]([CH3:14])[C:16](=[O:17])[NH:18][C:19]2=[O:20])[CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11]

Participants

Reactant 2

HCID 8655Syringaldehyde

HCID 692171-Methylhydantoin

Product 1

HCID 542950435-[(3,5-Dimethoxy-4-hydroxyphenyl)methylene]-1-methyl-2,4-imidazolidinedioneYield 33.5%

Procedure

Prepared according to the procedure described in Example 99 using 3,5-dimethoxy-4-hydroxybenzaldehyde (5.8 g, 31 mmoles) and 1-methyl hydantoin (3.5 g, 30 mmoles). Recrystallization from ethanol gave the pure product (2.8 g),mp 194°-196° C.

Workup

customPrepared
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-c9a1b2b0c8904399b4c66908e168e865
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464856

Reaction notes

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