Hydrochloric Acid → HCID 12972142, compound

HRID 1279286Notes

Reaction equation

HRID 1279286 reaction equation
[CH2:1]([O:3][C:4](OCC)=[C:5]([C:8](=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[C:6]#[N:7])[CH3:2].[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([Cl:34])[C:25]=1[NH:35][NH2:36].Cl>C(O)C>[NH2:7][C:6]1[N:35]([C:25]2[C:24]([Cl:23])=[CH:29][C:28]([C:30]([F:31])([F:33])[F:32])=[CH:27][C:26]=2[Cl:34])[N:36]=[C:4]([O:3][CH2:1][CH3:2])[C:5]=1[C:8](=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 18427787HCID 18427787, compound2×

Product 1

HCID 12972142HCID 12972142, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aliquot of the above solution of step A containing approximately two millimoles of 3,3-bis-ethoxy-2-(3-trifluoromethylbenzoyl)acrylonitrile was reacted with 0.49 g (2.0 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 10 mL of ethanol under reflux overnight. The cooled mixture was poured into dilute hydrogen chloride (HCl) and the product was extracted into ethyl acetate (EtOAc), washed with water and brine, and dried over magnesium sulfate (MgSO4). Chromatography on silica gel with 4:1 hexane/EtOAc gave the title product, 320 mg (31%), m.p. 77-78° C. from pentane.

Workup

  1. temperatureunder reflux overnight
  2. extractionthe product was extracted into ethyl acetate (EtOAc)
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate (MgSO4)

Sources & evidence

ORD record
ord-bf768c5feb7843558709f189f29f35e0
Source dataset
uspto-grants-2002_09
Patent number
US06448265B1

Reaction notes

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