Benzoylhydrazine → HCID 53791839, compound

HRID 1645958Notes

Reaction equation

HRID 1645958 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:12](=N)([O:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH2:15][CH3:16]>CCO>[C:1]([NH:9][N:10]=[C:12]([O:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH2:15][CH3:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11955BenzoylhydrazineHCID 12283341Ethyl pentanimidate hydrochloride

Product 1

HCID 53791839HCID 53791839, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.2 g (15.9 mmol) of benzoic hydrazide in 50 ml of dry EtOH was stirred under N2 at -10° C. as a solution of 2.5 g (15.1 mmol) of ethyl valerimidate hydrochloride [prepared by method of A. H. Hill and I. Rabinowitz, J. Am. Chem. Soc. 48, 734 (1926)] in 50 ml of dry EtOH was added dropwise over about 15 minutes. Stirring was continued at -10° C. for 3 hours, during which time a white precipitate separated. The cold mixture was filtered through Celite, and the filtrate was co-evaporated with CHCl3 at 10° C. The residue was chromatographed twice on silica gel columns (gradient elution with 0.3-5% MeOH in CH2Cl2) to give 951 mg (25%) of the title compound as a cream-colored semi-solid, suitable for use without further purification (TLC in 97:3 CH2Cl2 -MeOH). 1H NMR (CDCl3, 400 MHz) was complex, suggesting that the product is a mixture of syn- and anti-isomers.

Workup

  1. additionwas added dropwise over about 15 minutes
  2. customa white precipitate separated
  3. filtrationThe cold mixture was filtered through Celite
  4. customwas co-evaporated with CHCl3 at 10° C
  5. customThe residue was chromatographed twice on silica gel columns (gradient elution with 0.3-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7c067fcb98ba4ea4be215dae18ee174e
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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