Thiosemicarbazide → HCID 78165248, compound

HRID 333199Notes

Reaction equation

HRID 333199 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][NH:24][C:25]([NH2:27])=[S:26]>O1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1](=[N:23][NH:24][C:25]([NH2:27])=[S:26])([C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723789ThiosemicarbazideHCID 85856804HCID 85856804, compound

Product 1

HCID 78165248HCID 78165248, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-toluenesulfonic acid (0.007 g, 0.03 mmol) was added to a solution of 3-benzoyl benzhydrol 5 (0.396 g, 1.09 mmol) in anhydrous tetrahydrofuran (10 mL). After stirring at reflux for 10 min, thiosemicarbazide (0.199 g, 2.19 mmol) was added to the reaction mixture and stirred for 2 days under an inert atmosphere of nitrogen gas. After 2 days, tetrahydrofuran was removed under reduced pressure and water (50 mL) was added. The products were extracted with ethyl acetate (2×20 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 88:12 to 0:100) afforded 3-benzoyl benzhydrol thiosemicarbazone 6 (0.228 g, 0.631 mmol) as a white solid in a 57% yield. HRMS (ESI) calculated for C21H19N3OSH+ (M+H)+ 362.1321, found 362.1336.

Workup

  1. temperatureat reflux for 10 min
  2. stirringstirred for 2 days under an inert atmosphere of nitrogen gas
  3. customtetrahydrofuran was removed under reduced pressure and water (50 mL)
  4. additionwas added
  5. extractionThe products were extracted with ethyl acetate (2×20 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-f5e6fcb9d7b84f659819491ba6366688
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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