Acetohydrazide → HCID 13770444, compound

HRID 2049922Notes

Reaction equation

HRID 2049922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl>[C:16]([NH:19][NH:20][C:13]([C:11]1[O:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:15])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 14039AcetohydrazideHCID 7266935-(4-Chlorophenyl)-2-furoic acid

Product 1

HCID 13770444HCID 13770444, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 111.5 g (0.5 mole) of 5-(p-chlorophenyl)furoic acid in 500 ml of thionyl chloride was heated at reflux for 1-11/4 hr. After slight cooling, the reaction mixture was filtered and the filtrate was concentrated in a water bath at reduced pressure to a creamy solid. The solid was dissolved in 400 ml of chloroform. To this chloroform solution under stirring at room temperature was added a suspension of 74 g (1 mole) of acetyl hydrazine in 900 ml of chloroform. Addition was completed in about 20 min. White creamy solid separated fairly readily while the temperature rose to about 45°. The mixture was allowed to stir at ambient temperature overnight.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1-11/4 hr
  3. filtrationAfter slight cooling, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in a water bath at reduced pressure to a creamy solid
  5. dissolutionThe solid was dissolved in 400 ml of chloroform
  6. additionwas added
  7. additionAddition
  8. customWhite creamy solid separated fairly readily while the temperature
  9. customrose to about 45°
  10. stirringto stir at ambient temperature overnight

Sources & evidence

ORD record
ord-a6a7f905ce324c7f8c98205ea8b68799
Source dataset
uspto-grants-1980_04
Patent number
US04199508

Reaction notes

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