Ethyl Acetate → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone

HRID 2938

Reaction equation

HRID 2938 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70849Hantzsch esterHCID 30715115-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone

Product 1

HCID 99683565-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinoneYield 56.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere, 13.98 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone, 13.17 g of diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate and 600 ml of toluene were stirred to effect solution. Forty grams of silica gel 60 (finer than 230 mesh) previously dried in vacuo at 50° C. for 7 hours were added to the reaction. The reaction was heated at reflux for 18 hours and filtered hot. The filtrate was evaporated to dryness. The residue was dissolved in 500 ml of ethyl acetate, washed 5 times each with 400 ml of 1N hydrochloric acid, dried over sodium sulfate, filtered, and evaporated in vacuo to provide a yellow solid. Chromatography over silica gel eluting with 2.5% ethyl acetate in toluene provided 8.0 g of the desired title product, m.p. 178°-179° C.

Workup

  1. customForty grams of silica gel 60 (finer than 230 mesh) previously dried in vacuo at 50° C. for 7 hours
  2. additionwere added to the reaction
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 18 hours
  5. filtrationfiltered hot
  6. customThe filtrate was evaporated to dryness
  7. dissolutionThe residue was dissolved in 500 ml of ethyl acetate
  8. washwashed 5 times each with 400 ml of 1N hydrochloric acid
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customto provide a yellow solid

Sources & evidence

ORD record
ord-6c9be2f1c1414538a509efd6fbcd16ff
Source dataset
uspto-grants-1998_03
Patent number
US05731336

Linked notes

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