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

HRID 1464642Notes

Reaction equation

HRID 1464642 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-a6314add813544898e7b6ec291fcd298
Source dataset
uspto-grants-1994_04
Patent number
US05306822

Reaction notes

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