p-Toluenesulfonic acid → HCID 136045554, compound

HRID 652795Notes

Reaction equation

HRID 652795 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)([CH3:4])([CH3:3])[CH3:2].[NH2:24][NH:25][C:26]([NH2:28])=[S:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8](=[N:24][NH:25][C:26]([NH2:28])=[S:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1898376Methanone, [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenyl-HCID 2723789Thiosemicarbazide

Product 1

HCID 136045554HCID 136045554, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.2 g of 3,5-di-t-butyl-4-hydroxybenzophenone and 2.2 g of thiosemicarbazide were dissolved in 20 ml of toluene, and 0.4 g of p-toluenesulfonic acid was added. The solution was refluxed for 16 hours while removing water. After the reaction, dilute hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was distilled off under reduced pressure. The residue was chromatographed on a silica gel column, and recrystallized from dichloromethane/n-hexane to give 3,5-di-t-butyl-4-hydroxybenzophenone thiosemicarbazone.

Workup

  1. temperatureThe solution was refluxed for 16 hours
  2. customwhile removing water
  3. customAfter the reaction, dilute hydrochloric acid
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was chromatographed on a silica gel column
  10. customrecrystallized from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-0fae368c7edf4e358cee98f4b142cb0f
Source dataset
uspto-grants-1987_06
Patent number
US04673692

Reaction notes

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