Semicarbazide hydrochloride → HCID 53851367, compound

HRID 262524Notes

Reaction equation

HRID 262524 reaction equation
[N+:1]([C:4]1[O:5][C:6]2[C:18]([CH:19]=O)=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2].Cl.[NH2:22][NH:23][C:24]([NH2:26])=[O:25].C([O-])(=O)C.[Na+]>C(O)C>[N+:1]([C:4]1[O:5][C:6]2[C:18]([CH:19]=[N:22][NH:23][C:24]([NH2:26])=[O:25])=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 20195518HCID 20195518, compound

Product 1

HCID 53851367HCID 53851367, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2.1 g. (0.0079 mole) of 2-nitro-3-phenylbenzofuran-7-carboxaldehyde in 70 ml. of ethanol is added 1.34 g. (0.012 mole) of semicarbazide hydrochloride and 1.07 g. (0.013 mole) of sodium acetate. The mixture is heated to its reflux temperature and maintained at reflux for 3 hours. The precipitated product is separated by filtration, washed with water and diethyl ether. The solid is washed with hot dichloroethane, separated by filtration, then dissolved in a mixture of 650 ml. of chloroform and 100 ml. of acetone by heating. This solution is washed twice with water, once with sodium bicarbonate solution, again with water, once with dilute hydrochloric acid, and twice with water. The solution is dried and the dry solution is evaporated to provide solid 2-nitro-3-phenylbenzofuran-7-carboxaldehyde semicarbazone, m.p. 249° C. (dec.).

Workup

  1. additionTo a mixture of 2.1 g
  2. temperatureThe mixture is heated to its
  3. temperaturereflux temperature
  4. temperaturemaintained
  5. temperatureat reflux for 3 hours
  6. customThe precipitated product is separated by filtration
  7. washwashed with water and diethyl ether
  8. washThe solid is washed with hot dichloroethane
  9. customseparated by filtration
  10. dissolutiondissolved in a mixture of 650 ml
  11. temperatureof acetone by heating
  12. washThis solution is washed twice with water, once with sodium bicarbonate solution, again with water, once with dilute hydrochloric acid
  13. customThe solution is dried
  14. customthe dry solution is evaporated

Sources & evidence

ORD record
ord-e3546252d9ba455fb2398389153bec44
Source dataset
uspto-grants-1979_05
Patent number
US04154847

Reaction notes

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