p-Toluenesulfonic acid → 1-(3-Methylbenzoyl),3-(3-methylbenzoyl)benzene thiosemicarbazone

HRID 333201Notes

Reaction equation

HRID 333201 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][CH:35]=1)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=2)[CH:19]=1)=[O:17].[NH2:36][NH:37][C:38]([NH2:40])=[S:39]>CO>[CH3:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][CH:35]=1)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](=[N:36][NH:37][C:38]([NH2:40])=[S:39])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=2)[CH:19]=1)=[O:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2723789ThiosemicarbazideHCID 541772461-(3-Methylbenzoyl),3-(3-methylbenzoyl)benzene

Product 1

HCID 781652491-(3-Methylbenzoyl),3-(3-methylbenzoyl)benzene thiosemicarbazoneYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-toluenesulfonic acid (0.018 g, 0.09 mmol) was added to a solution of 1-(3-methylbenzoyl),3-(3-methylbenzoyl)benzene 8 (0.300 g, 0.95 mmol) in anhydrous methanol (10 mL). After stirring at reflux for 10 min, thiosemicarbazide (0.086 g, 0.954 mmol) was added to the reaction mixture and stirred for 12 h under an inert atmosphere of nitrogen gas. After 12 h, methanol was removed under reduced pressure and 10 mL of water was then added. The products were extracted with dichloromethane (2×30 mL) and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 90:10 to 80:20) afforded 1-(3-methylbenzoyl),3-(3-methylbenzoyl)benzene thiosemicarbazone 9 (0.063 g, 0.016 mmol) as a white solid in a 17% yield. HRMS (ESI) calculated for C23H21N3OSH+ (M+H)+ 388.14781, found 388.14793. The product was determined to be approximately 80% pure and was submitted for biological testing without further purification.

Workup

  1. temperatureat reflux for 10 min
  2. stirringstirred for 12 h under an inert atmosphere of nitrogen gas
  3. custommethanol was removed under reduced pressure and 10 mL of water
  4. additionwas then added
  5. extractionThe products were extracted with dichloromethane (2×30 mL)
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-3ad2deb1d07d4cb89faca29f27fbf6b4
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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