4-Pyridinecarboxaldehyde → Phenyl (4-pyridinylmethylene)carbazate monohydrochloride

HRID 1085956Notes

Reaction equation

HRID 1085956 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[ClH:9].[C:10]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:13])[NH:11][NH2:12]>C(O)C>[ClH:9].[N:1]1[CH:2]=[CH:3][C:4]([CH:7]=[N:12][NH:11][C:10]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 19830215Phenyl carbazate hydrochloride

Product 1

HCID 86744747Phenyl (4-pyridinylmethylene)carbazate monohydrochlorideYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.43 gm (0.06 mole) of 4-pyridinecarboxaldehyde, 11.31 gm (0.06 mole) of phenyl carbazate hydrochloride and 300 ml of 95% ethanol is refluxed 4 hr. The reaction mixture is evaporated to dryness. The crude product is suspended in 200 ml of boiling absolute ethanol and sufficient methanol added to give a solution. The hot solution is filtered, the filtrate cooled to room temperature and then chilled in the freezer. The crystals are collected, washed with Skellysolve B and dried to yield 11.0 gm (66%) of the title compound having a melting point of 224.4° C. (decomp).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. additionadded
  3. customto give a solution
  4. filtrationThe hot solution is filtered
  5. temperaturechilled in the freezer
  6. customThe crystals are collected
  7. washwashed with Skellysolve B
  8. customdried

Sources & evidence

ORD record
ord-f0130a0d21a149f89c9619a021814b79
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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