Acetic Acid → 5-Methoxycarbonylfuryl phenyl ketone benzylhydrazone

HRID 2225019Notes

Reaction equation

HRID 2225019 reaction equation
[C:1]1([C:7]([C:9]2[O:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C>CO>[CH2:18]([NH:25][N:26]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[O:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11157(Phenylmethyl)hydrazineHCID 107757905-Benzoyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 731119045-Methoxycarbonylfuryl phenyl ketone benzylhydrazone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxycarbonyl-2-furyl phenyl ketone (5.5 g, 0.024 mole) was dissolved in methanol (60 ml), added with benzylhydrazine (9 g, 0.07 mole) and acetic acid (0.5 ml) and then heated under reflux till the reaction was completed. After cooling, the solvent was evaporated. The resultant residue was extracted with chloroform and washed with dilute HCl solution, then water, and then dried over anhydrous magnesium sulfate and filtered. The solvent of the filtrate was removed to give 5-methoxycarbonylfuryl phenyl ketone benzylhydrazone.

Workup

  1. temperatureheated
  2. temperatureunder reflux till the reaction
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. extractionThe resultant residue was extracted with chloroform
  6. washwashed with dilute HCl solution
  7. dry with materialwater, and then dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent of the filtrate was removed

Sources & evidence

ORD record
ord-cd43826d3f534bd9bd4fbb75164f4ba1
Source dataset
uspto-grants-2008_05
Patent number
US07378532B2

Reaction notes

Loading…