(2,4-Dichlorophenyl)hydrazine monohydrochloride → HCID 24887407, compound

HRID 1875854Notes

Reaction equation

HRID 1875854 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[CH:20]([S:28][CH3:29])[C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:14]=1>C(O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:10]([C:4]3[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=3[Cl:2])[N:11]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]=2[S:28][CH3:29])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2723905(2,4-Dichlorophenyl)hydrazine monohydrochlorideHCID 67322357HCID 67322357, compound

Product 1

HCID 24887407HCID 24887407, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 15.6 g of 2,4-dichlorophenylhydrazine hydrochloride (5) in mL of ethanol was added 22 g of ethyl 4-(4-chlorophenyl)-3-(methylthio)-2,4-dioxobutanoate (4) in 120 mL of ethanol at room temperature. After 2 hours, the mixture was refluxed for 15 hours and then cooled to the room temperature. The mixture was filtered off and the filtrate was evaporated off under the reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: hexane/EtOAc mixture (80/20; v/v) to obtain 25 g of the title compound as pale orange color solid.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. filtrationThe mixture was filtered off
  3. customthe filtrate was evaporated off under the reduced pressure

Sources & evidence

ORD record
ord-e3092667d68744d897b677562d33ec60
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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