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

HRID 128733

Reaction equation

HRID 128733 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-94182eba54ee4fcc8316740632dfd6a6
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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