Acetic Acid → HCID 21918729, compound

HRID 987045Notes

Reaction equation

HRID 987045 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])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N+:18]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(O)(=O)C.[SH:32][CH2:33][C:34](O)=[O:35]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]2[N:25]([C:24]3[CH:26]=[CH:27][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=3)[C:34](=[O:35])[CH2:33][S:32]2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1133Thioglycolic AcidHCID 74754-NitroanilineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 21918729HCID 21918729, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g of 3,5-di-t-butyl-4-hydroxybenzaldehyde (21 mmol) and 2.95 g of para-nitroaniline (21 mmol) are dissolved in 50 ml of anhydrous toluene. 0.5 ml of glacial acetic acid is added and the whole is taken to reflux for 24 hours. Then 1.96 g of mercaptoacetic acid (21 mmol) is added to the medium and reflux is continued for another 24 hours. After the reaction mixture has returned to ambient temperature, it is washed with water (3 times 30 ml). After decantation, the organic phase is dried over sodium sulphate and the solvent is evaporated off under reduced pressure. The residue is purified on silica gel in an ethyl acetate/heptane mixture (1/4) and 1.33 g of pure 2-(3,5-di-t-butyl-4-hydroxyphenyl)-3-(4-nitrophenyl)-4-thiazolidinone is obtained in the form of a colourless oil (15%).

Workup

  1. temperatureto reflux for 24 hours
  2. temperaturereflux
  3. customhas returned to ambient temperature
  4. washit is washed with water (3 times 30 ml)
  5. dry with materialAfter decantation, the organic phase is dried over sodium sulphate
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe residue is purified on silica gel in an ethyl acetate/heptane mixture (1/4)

Sources & evidence

ORD record
ord-a8d133d0165541e9adfd4c1345f28277
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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