p-Toluenesulfonic acid → HCID 72486478, compound

HRID 253961Notes

Reaction equation

HRID 253961 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:5]([Cl:8])=[N:6][CH:7]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[NH:21][NH2:22].CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:25]([O:24][C:20]([NH:21][N:22]=[C:9]([C:4]1[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[Cl:18])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 58179505HCID 58179505, compound

Product 1

HCID 72486478HCID 72486478, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)ethanone (1.14 g, 3.03 mmol) in EtOH (40 mL) was added ethyl carbazate (0.95 g, 9.09 mmol) and TsOH (2 mg). The reaction mixture was heated for 3 hours, followed by evaporated of the volatiles to give ethyl-2-(1-(5-bromo-2-chloropyridin-3-yl)-2-(2,3-dichlorophenyl)ethylidene)hydrazinecarboxylate as a yellow oil, which was used directly in the next step.

Workup

  1. temperatureThe reaction mixture was heated for 3 hours
  2. customby evaporated of the volatiles

Sources & evidence

ORD record
ord-1c89c6dbb385491aa32890a104d336c0
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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