4-Acetylpyridine → Phenyl [1-(4-pyridinyl)ethylidene]carbazate monohydrochloride

HRID 1085953Notes

Reaction equation

HRID 1085953 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[ClH:10].[C:11]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])[NH:12][NH2:13]>C(O)C>[ClH:10].[N:7]1[CH:8]=[CH:9][C:4]([C:1](=[N:13][NH:12][C:11]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[CH3:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 142824-AcetylpyridineHCID 19830215Phenyl carbazate hydrochloride

Product 1

HCID 86744746Phenyl [1-(4-pyridinyl)ethylidene]carbazate monohydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.11 gm (0.1 mole) of 4-acetylpyridine, 18.85 gm (0.1 mole) of phenyl carbazate hydrochloride and 250 ml of absolute ethanol is refluxed 6 hr and cooled. The reaction mixture is evaporated to dryness in vacuo to give a rose-colored solid. The crude product is crystallized from absolute ethanol to yield 28.13 gm (97%) of the title compound having a melting point of 159.1° C.

Workup

  1. temperatureis refluxed 6 hr
  2. temperaturecooled
  3. customThe reaction mixture is evaporated to dryness in vacuo
  4. customto give a rose-colored solid
  5. customThe crude product is crystallized from absolute ethanol

Sources & evidence

ORD record
ord-3f338981cf634822b7248b2d59c67868
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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