[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → [5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methylsulfanyl-1H-pyrazol-4-yl]-(2,5-dimethylphenyl)methanone

HRID 2305760Notes

Reaction equation

HRID 2305760 reaction equation
CS[C:3]([S:17][CH3:18])=[C:4]([C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15])[C:5]#[N:6].[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([Cl:30])[C:21]=1[NH:31][NH2:32]>C(O)C>[NH2:6][C:5]1[N:31]([C:21]2[C:22]([Cl:30])=[CH:23][C:24]([C:26]([F:27])([F:28])[F:29])=[CH:25][C:20]=2[Cl:19])[N:32]=[C:3]([S:17][CH3:18])[C:4]=1[C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15]

Participants

4

Reactant 2

HCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952653,3-Bis-methylthio-2-(2,5-dimethylbenzoyl)-acrylonitrile

Product 1

HCID 10183914[5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methylsulfanyl-1H-pyrazol-4-yl]-(2,5-dimethylphenyl)methanoneYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7.94 g (28.6 mmol) of the product of step C and 7.01 g (28.6 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 100 mL of ethanol was heated at reflux for 2 hours, solution occurring as the reaction mixture was warmed. Then the ethanol was mostly removed on the rotary evaporator and the residues were partitioned between dilute aqueous hydrogen chloride solution and ethyl acetate. The organic phase was washed once with water and with brine, then dried with magnesium sulfate and treated with decolorizing carbon. The filtered solution was evaporated and the residues crystallized from 10:1 hexane/ethyl acetate to give 12.00 g (88%) of the title product in two crops, m.p. 130-132° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturewas warmed
  4. customThen the ethanol was mostly removed on the rotary evaporator
  5. customthe residues were partitioned between dilute aqueous hydrogen chloride solution and ethyl acetate
  6. washThe organic phase was washed once with water and with brine
  7. dry with materialdried with magnesium sulfate
  8. additiontreated with decolorizing carbon
  9. customThe filtered solution was evaporated
  10. customthe residues crystallized from 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-82dea0b07cbc42479c385e3c9dfb1f55
Source dataset
uspto-grants-2002_08
Patent number
US06441018B2

Reaction notes

Loading…