Acetophenone → Acetophenone benzoylhydrazone

HRID 22098

Reaction equation

HRID 22098 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12]>O1CCCC1>[C:1]([NH:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 11955Benzoylhydrazine

Product 1

HCID 346107Acetophenone benzoylhydrazone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of benzoic acid hydrazide (5.70 g, 0.042 mol) in tetrahydrofuran (75 mL) was added acetophenone (5.5 g, 0.046 mol) followed by concentrated. HCl (3 drops). The reaction was allowed to stir for 12 h at 25° C. during which time the product precipitated as a colorless crystalline solid. The product was filtered, washed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL), and the crystalline solids were dried in vacuo (6.65 g, 64%). 1H NMR (CD2Cl2): δ2.35 (s, 3H, CH3), 7.30-8.0 (m, 10H, Ph), 9.0 (br, 1H, NH). All other substrates were prepared in a similar fashion.

Workup

  1. concentrationby concentrated
  2. customprecipitated as a colorless crystalline solid
  3. filtrationThe product was filtered
  4. washwashed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL)
  5. customthe crystalline solids were dried in vacuo (6.65 g, 64%)
  6. customAll other substrates were prepared in a similar fashion

Sources & evidence

ORD record
ord-0b866c1b184048648795054c228cf6bd
Source dataset
uspto-grants-1995_06
Patent number
US05426223

Linked notes

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