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

HRID 1085952Notes

Reaction equation

HRID 1085952 reaction equation
Cl.[C:2]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:5])[NH:3][NH2:4].[C:13]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)(=O)[CH3:14].C(O)C>O>[N:19]1[CH:20]=[CH:21][C:16]([C:13](=[N:4][NH:3][C:2]([O:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:5])[CH3:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 142824-AcetylpyridineHCID 19830215Phenyl carbazate hydrochloride

Product 1

HCID 53675283Phenyl [1-(4-pyridinyl)ethylidene]carbazateYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5.66 gm (0.03 mole) of phenyl carbazate hydrochloride, 3.63 gm (0.03 mole) of 4-acetylpyridine and 50 ml of ethanol is refluxed 2 hr. The solution is cooled and evaporated to dryness in vacuo to give an oil. The oil is triturated with ethyl acetate-methanol to afford a solid. The solid is dissolved in 50 ml of water and treated with 50 ml water containing 5 gm sodium carbonate. A gummy solid separates which solidifies on standing. The crude product is collected and crystallized from ethyl acetate-Skellysolve B to yield 4.13 gm (54%) of the title compound having a melting point of 120.4° C. (decomp.).

Workup

  1. temperatureThe solution is cooled
  2. customevaporated to dryness in vacuo
  3. customto give an oil
  4. customThe oil is triturated with ethyl acetate-methanol
  5. customto afford a solid
  6. customThe crude product is collected
  7. customcrystallized from ethyl acetate-Skellysolve B

Sources & evidence

ORD record
ord-98e555d105de4da7a577ce9678508e30
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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