3,5-Dibromo-4-Hydroxybenzaldehyde → 5-[(3,5-Dibromo-4-hydroxyphenyl)methylene]-2-thioxo-4-imidazolidinone

HRID 128732

Reaction equation

HRID 128732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])[CH:5]=O.[NH:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[S:14].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:18]2[NH:12][C:13](=[S:14])[NH:15][C:16]2=[O:17])[CH:7]=[C:8]([Br:11])[C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 517045Sodium AcetateHCID 12740302-Thiohydantoin

Product 1

HCID 28660855-[(3,5-Dibromo-4-hydroxyphenyl)methylene]-2-thioxo-4-imidazolidinoneYield 24.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to the procedure described in Example 1 using 3,5-dibromo-4-hydroxybenzaldehyde (4.5 g, 16 mmoles), 2-thiohydantoin (1.7 g, 15 mmoles), sodium acetate (4.5 g, 55 mmoles), and acetic acid (35 ml). Recrystallization from ethanol gave the pure product (1.4 g), mp 267° C. (dec).

Workup

  1. customPrepared
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-628e0f9dcd8f4aa5bb2a85c7ec74e74a
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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