Semicarbazide hydrochloride → HCID 12339322, compound

HRID 1708428Notes

Reaction equation

HRID 1708428 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].C[O-].[Na+].[C:10]([CH2:18][C:19]#[N:20])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[NH2:20][C:19]1[N:3]([C:4]([NH2:6])=[O:5])[N:2]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 64799BenzoylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 12339322HCID 12339322, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6.0 g of semicarbazide hydrochloride in 100 ml of ethyl alcohol is added 2.8 g of sodium methoxide at room temperature. The reaction mixture is stirred for 10 minutes and 7.0 g of benzoylacetonitrile added. The reaction mixture is heated at reflux for 1 hour, cooled and concentrated in vacuo to a yellow solid. The yellow solid is suspended in water, filtered and dried. The dried solid is suspended in 100 ml of ethyl alcohol and 10 ml of triethylamine followed by heating at reflux for 1 hour. The reaction mixture is cooled and the volatiles removed in vacuo to a residue which is suspended in water, filtered, washed with water and dried to give 5.0 g of the desired product as a solid, m.p. 255° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated in vacuo to a yellow solid
  5. filtrationfiltered
  6. customdried
  7. temperatureby heating
  8. temperatureat reflux for 1 hour
  9. temperatureThe reaction mixture is cooled
  10. customthe volatiles removed in vacuo to a residue which
  11. filtrationfiltered
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-5fa34ac757fc4d949a0ca1b6becd149d
Source dataset
uspto-grants-1994_10
Patent number
US05358947

Reaction notes

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