Hydrazine hydrate (1:1) → HCID 178489651, compound

HRID 1471882Notes

Reaction equation

HRID 1471882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[C:18](SC)[S:19][CH3:20])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1.O.[NH2:24][NH2:25]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:24][NH:25][C:18]=2[S:19][CH3:20])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 86657578HCID 86657578, compound

Product 1

HCID 178489651HCID 178489651, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-3,3-bis(methylthio)-1-phenylprop-2-en-1-one in EtOH (100 mL) was added hydrazine hydrate (5.36 mL, 110 mmol). The reaction mixture was refluxed overnight, additional hydrazine hydrate (1.00 mL, 20.6 mmol) was added, and the mixture was refluxed until the reaction was complete. The mixture was concentrated under reduced pressure, washed with H2O and extracted with CH2Cl2. The combined organic layers were washed with H2O, brine, dried over MgSO4 and concentrated to give the title compound (6.67 g). LCMS m/z=397 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturethe mixture was refluxed until the reaction
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washwashed with H2O
  5. extractionextracted with CH2Cl2
  6. washThe combined organic layers were washed with H2O, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-19b0c852b44e4dd08949ed329df95bef
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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