4-Chlorobenzohydrazide → 2-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide

HRID 660893Notes

Reaction equation

HRID 660893 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([N:15]=[C:16]=[O:17])[CH:13]=[CH2:14]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:16]([NH:15][CH2:12][CH:13]=[CH2:14])=[O:17])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108164-ChlorobenzohydrazideHCID 15123Allyl isocyanate

Product 1

HCID 497656012-(4-chlorobenzoyl)-N-allylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere, 19.00 g (111.4 mmol) of 4-chlorobenzoic acid hydrazide are placed in 150 ml THF. 9.44 g (111.6 mmol) of allyl isocyanate, dissolved in 110 ml THF, are added dropwise at 50° C. and the mixture further stirred overnight at 50° C. The solvent is then evaporated in vacuo, diethyl ether is added to the residue and the solid formed is isolated and purified by filtration and further washing with diethyl ether. 26.80 g (95% of theory) of the target compound are thus obtained.

Workup

  1. additionare added dropwise at 50° C.
  2. customThe solvent is then evaporated in vacuo, diethyl ether
  3. additionis added to the residue
  4. customthe solid formed
  5. customis isolated
  6. filtrationpurified by filtration
  7. washfurther washing with diethyl ether
  8. custom26.80 g (95% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-0c58f86614bb4a259ba6cadce5f07b27
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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