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Hydrazine → 4-chloro-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carbohydrazide

HRID 254817
Notes
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Reaction equation

HRID 254817 reaction equation
[Cl:1][C:2]1[C:3]([C:22]([O:24]CC)=O)=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[NH2:27][NH2:28]>C(O)C>[Cl:1][C:2]1[C:3]([C:22]([NH:27][NH2:28])=[O:24])=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66844323ethyl 4-chloro-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 668453014-chloro-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 4-chloro-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate (3.1 g, 7.2 mmol) in ethyl alcohol (30 ml) was added hydrazine (5 ml, 64% solution in water) in one portion. The reaction mixture was refluxed 100° C. for 6 hours, and then cooled down to room temperature. After volatile solvent was removed in reduced pressure, the residue was purified with silica gel column (5% methanol in methylene chloride) to obtained title compound (3 g, quantitatively) as slightly yellow solid.

Workup

  1. temperaturecooled down to room temperature
  2. customAfter volatile solvent was removed in reduced pressure
  3. customthe residue was purified with silica gel column (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-6391b7d7d6a443d385455059517a809c
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07875647B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes