4-Chlorobenzohydrazide → HCID 47133870, compound

HRID 660838Notes

Reaction equation

HRID 660838 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.[CH:12]1([N:15]=[C:16]=[O:17])[CH2:14][CH2:13]1>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:16]([NH:15][CH:12]2[CH2:14][CH2:13]2)=[O:17])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108164-ChlorobenzohydrazideHCID 637659Isocyanatocyclopropane

Product 1

HCID 47133870HCID 47133870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere, 4.00 g (23.4 mmol) of 4-chlorobenzoic acid hydrazide are placed in 50 ml tetrahydrofuran. 1.95 g (23.4 mmol) of cyclopropyl isocyanate, dissolved in 50 ml tetrahydrofuran, are added dropwise at 50° C., and the mixture further stirred overnight at 50° C. The solvent is 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. 5.92 g (ca. 100% of theory) of the target compound are thus obtained.

Workup

  1. additionare added dropwise at 50° C.
  2. customThe solvent is 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. custom5.92 g (ca. 100% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-814020fe38114f1f9d9dedf11305c678
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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