Vanillin → 5-[(4-Hydroxy-3-methoxyphenyl)methylene]-3-methyl-2,4-imidazolidinedione

HRID 128741Notes

Reaction equation

HRID 128741 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].[CH3:12][N:13]1[C:17](=[O:18])[CH2:16][NH:15][C:14]1=[O:19]>>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:16]2[NH:15][C:14](=[O:19])[N:13]([CH3:12])[C:17]2=[O:18])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

3

Reactant 2

HCID 1183VanillinHCID 1388512,4-Imidazolidinedione, 3-methyl-

Product 1

HCID 544966765-[(4-Hydroxy-3-methoxyphenyl)methylene]-3-methyl-2,4-imidazolidinedioneYield 13.4%

Procedure

Prepared according to the procedure described in Example 93 using 4-hydroxy-3-methoxybenzaldehyde (3.2 g, 21 mmoles) and 3-methyl hydantoin (3.0 g, 21 mmoles). Recrystallization from ethyl acetate gave the pure product (0.7 g), mp 227°-228° C.

Workup

  1. customPrepared
  2. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-de6ee6f4af1a4b818848694ea2fb696b
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Reaction notes

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