Water → HCID 21188137, compound

HRID 1383592Notes

Reaction equation

HRID 1383592 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]#[CH:22].C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.O.CCOCC>C(#N)C>[C:21]([C:3]1[C:4]([C:19]#[N:20])=[N:5][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:11][C:12]=2[Cl:13])[C:2]=1[NH2:1])(=[O:30])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 9950049HCID 9950049, compound

Product 1

HCID 21188137HCID 21188137, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-ethynylpyrazole (0.345 g) in acetonitrile (5 ml) was added p-toluenesulphonic acid (0.5 g) and the mixture was stirred at room temperature for 2 hours and then poured into water (100 ml) and ether (100 ml). The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml), brine (50 ml), dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluted with dichloromethane: hexane (10:1). Combination and evaporation of suitable fractions gave the title compound as a white crystalline solid, m.p. 200-201° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution (50 ml), brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (40 g)
  6. washeluted with dichloromethane: hexane (10:1)
  7. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-6157717cd3654dc48952f59b6642392f
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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