Water → HCID 178503593, compound

HRID 1471936Notes

Reaction equation

HRID 1471936 reaction equation
[CH3:1][S:2][C:3](SC)=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.O.[NH2:22][NH2:23].O>C(O)C>[CH3:1][S:2][C:3]1[NH:23][N:22]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 12412401HCID 12412401, compound

Product 1

HCID 178503593HCID 178503593, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3,3-bis(methylthio)-1,2-diphenylprop-2-en-1-one (2.5 g, 8.32 mmol) in ethanol (20 mL), was added hydrazine hydrate (1.67 g, 33.3 mmol) at room temperature. The reaction was refluxed for 6 h. After cooling, the reaction was poured into water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography to give the title compound (1.98 g). LCMS m/z=267.0 [M+H]+.

Workup

  1. temperatureThe reaction was refluxed for 6 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d957c2071194524a84c8b33c6b8ab24
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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