3,5-Di-tert-butyl-4-hydroxybenzaldehyde → 2-Amino-5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4(5H)-thiazolone

HRID 2396803Notes

Reaction equation

HRID 2396803 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])C=O)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(/[CH:32]=[C:33]2/[C:34]([NH:36][C:37]([S:39]/2)=[NH:38])=[O:35])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:3][C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[C:33]2[S:39][C:37](=[NH:38])[NH:36][C:34]2=[O:35])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 517045Sodium AcetateHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 1372447292-Amino-5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4(5H)-thiazoloneYield 70.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (9.4 g, 0.04 mole), pseudothiohydantoin (4.7 g, 0.0405 mole), sodium acetate (8.3 g, 0.1 mole), and glacial acetic acid (200 mL) is stirred and heated at reflux for 21 hours. The cooled mixture is added to ice-water and the precipitated solid is filtered and washed with water. The solid residue is dissolved in ether and washed successively with water, aqueous sodium bicarbonate solution, and water. The extract is dried and the solvent is removed to give 9.4 g of a residue. The crude product is recrystallized from methanol-ethyl acetate to give 3.8 g (38%) of 5-[[3,5-Bis(1,1-dimethylethyl)-4hydroxyphenyl]methylene]-2-imino-4-thiazolidinone, (Z)-, mp 277°-279° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 21 hours
  3. filtrationthe precipitated solid is filtered
  4. washwashed with water
  5. dissolutionThe solid residue is dissolved in ether
  6. washwashed successively with water, aqueous sodium bicarbonate solution, and water
  7. customThe extract is dried
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-6531ecc567be4c2a84db353d1868b9dc
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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