1-Acetyl-2-phenylhydrazine → HCID 10702980, compound

HRID 1890148Notes

Reaction equation

HRID 1890148 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].Br[CH:13]([OH:15])[CH3:14].C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[C:1]([NH:4][N:5]([CH2:14][CH2:13][OH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 82471-Acetyl-2-phenylhydrazineHCID 81531DiisopropylethylamineHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 10702980HCID 10702980, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-acetyl-2-phenylhydrazine (2 g, 13.3 mmol) in anhydrous toluene 20 ml was added bromoethanol (1.04 ml, 14.6 mmol), diisopropylethylamine (2.54 ml, 14.6 ml) at room temperature. The reaction mixture was refluxed under nitrogen for 40 hours. After cooling, the reaction was then quenched with 100 ml water, extracted with dichloromethane 2×100 ml. The organic was dried (MgSO4) and removed in vacuo. The residue was purified by flash column chromatography over silica using a gradient 50% mixture of ethyl acetate and hexane to 100% ethyl acetate as eluant. Appropriate fractions were combined and the solvent was removed in vacuo to give the product as a yellow oil 0.9 g (Yield 35%).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 40 hours
  2. temperatureAfter cooling
  3. customthe reaction was then quenched with 100 ml water
  4. extractionextracted with dichloromethane 2×100 ml
  5. dry with materialThe organic was dried (MgSO4)
  6. customremoved in vacuo
  7. customThe residue was purified by flash column chromatography over silica using a gradient 50% mixture of ethyl acetate and hexane to 100% ethyl acetate as eluant
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4cd4100b44154dbaa0d60b27da16ae49
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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