Ethanol → HCID 54230349, compound

HRID 1493703Notes

Reaction equation

HRID 1493703 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([CH2:9][CH2:10][CH2:11][CH3:12])=O)=[CH:3][CH:2]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[NH:14][NH2:15].C(O)C>C1(C)C=CC(S(O)(=O)=O)=CC=1.CO.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[N:15][NH:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 743441-Pentanone, 1-(4-pyridyl)-

Product 1

HCID 54230349HCID 54230349, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 8.3 gm (0.055 mole) of n-butyl 4-pyridinyl ketone, 6.1 gm (0.059 mole) of ethyl carbazate and 150 ml of absolute ethanol is refluxed 17 hr. A Tlc (3% MeOH/CH2Cl2 on Silica gel) shows 50% starting material remaining. p-Toluenesulfonic acid (0.3 gm) is added and the reaction mixture refluxed 17 hr more. Tlc shows no remaining starting materials. The reaction is concentrated in vacuo. The residue is slurried with water and the solid collected, washed with water and dried. Crystallization yields 7.41 gm of the title compound having a melting point of 102.1° C.

Workup

  1. temperatureis refluxed 17 hr
  2. temperaturethe reaction mixture refluxed 17 hr more
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe solid collected
  5. washwashed with water
  6. customdried
  7. customCrystallization

Sources & evidence

ORD record
ord-d41092764c69437a8c870910587c868f
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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