Diethyl Ether → 3,4-Dichlorobenzhydrazide

HRID 1834877Notes

Reaction equation

HRID 1834877 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)C.O.[NH2:15][NH2:16].C(OCC)C>C(O)C>[Cl:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Cl:11])[C:4]([NH:15][NH2:16])=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 11481387ethyl-3,4-dichlorobenzoate

Product 1

HCID 3119963,4-DichlorobenzhydrazideYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.5g (0.08 mol) of 3,4-dichlorobenzoic ethyl ester and 4.3g (0.086 mol) of 100%-hydrazine hydrate in 30 ml of ethanol were refluxed under heat for 6.5 hours. Upon cooled, the sedimented white crystals were added with ethyl ether and the reaction mixture was enough agitated and pulverized. The thus resulted products were filtered and enough washed with ethyl ether to provide 9.3g of 3,4-dichlorobenzoic hydrazide in white crystals. m.p.: 168°-170° C. Yield: 57%.

Workup

  1. temperatureunder heat for 6.5 hours
  2. temperatureUpon cooled
  3. filtrationThe thus resulted products were filtered
  4. washenough washed with ethyl ether

Sources & evidence

ORD record
ord-14e4908dcf784a8e85d7a881440363ce
Source dataset
uspto-grants-1978_01
Patent number
US04071633

Reaction notes

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