Methanone, 1,3-phenylenebis[phenyl- → HCID 78160443, compound

HRID 333196Notes

Reaction equation

HRID 333196 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][NH:24][C:25]([NH2:27])=[S:26]>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15](=[N:23][NH:24][C:25]([NH2:27])=[S:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 77388Methanone, 1,3-phenylenebis[phenyl-HCID 2723789Thiosemicarbazide

Product 1

HCID 78160443HCID 78160443, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

p-toluenesulfonic acid (0.026 g, 0.02 mmol) was added to a solution of 1,3 dibenzoylbenzene 2 (2.00 g, 6.98 mmol) in anhydrous methanol (20 mL). After stirring at reflux for 10 min, thiosemicarbazide (0.476 g, 5.235 mmol) was added to the reaction mixture and stirred for 26 h under an inert atmosphere of nitrogen gas. After 26 h, methanol was removed under reduced pressure and 50 mL of water was then added. The products were extracted with ethyl acetate (2×50 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 52:48) afforded 3-benzoyl benzophenone thiosemicarbazone 3 (0.829 g, 5.235 mmol) as a light yellow solid in a 44% yield. HRMS (ESI) calculated for C21H17N3OSH+ (M+H)+ 360.11651, found 360.11654. The isolated product 3 was 99.3% pure by HPLC at 300 and 320 nm; retention time 7.225 (method: 0-25 min, 50 to 100% acetonitrile, 50 to 0% water). This purified product was submitted for biological testing.

Workup

  1. temperatureat reflux for 10 min
  2. stirringstirred for 26 h under an inert atmosphere of nitrogen gas
  3. custommethanol was removed under reduced pressure and 50 mL of water
  4. additionwas then added
  5. extractionThe products were extracted with ethyl acetate (2×50 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-9c6a7c0b78544395b8411cc4b83960d6
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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