4-Hydroxy-3,5-bis(isopropyl)benzaldehyde → 5-[[4-Hydroxy-3,5-bis(1-methylethyl)phenyl]methylene]-2-thioxo-4-imidazolidinone

HRID 247871

Reaction equation

HRID 247871 reaction equation
[OH:1][C:2]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH:13]([CH3:15])[CH3:14].[NH:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[S:18].C([O-])(=O)C.[Na+]>C(O)(=O)C>[OH:1][C:2]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][C:5]([CH:6]=[C:22]2[NH:16][C:17](=[S:18])[NH:19][C:20]2=[O:21])=[CH:4][C:3]=1[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 517045Sodium AcetateHCID 12740302-Thiohydantoin

Product 1

HCID 539462155-[[4-Hydroxy-3,5-bis(1-methylethyl)phenyl]methylene]-2-thioxo-4-imidazolidinoneYield 32.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to the procedure described in Example 1 using 4-hydroxy-3,5-bis(1-methylethyl)benzaldehyde (3.0 g, 15 mmoles), 2-thiohydantoin (1.6 g, 14 mmoles), sodium acetate (4.2 g, 51 mmoles), and acetic acid (35 ml), filtered off, dried, and recrystallized from acetonitrile to afford the pure product (1.4 g), mp 225°-230° C.

Workup

  1. customPrepared
  2. filtrationfiltered off
  3. customdried
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-6d636aa34e82411b930dd679a966a56a
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Linked notes

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