Sodium Bicarbonate → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-propanoylpyrazole

HRID 377659Notes

Reaction equation

HRID 377659 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]#[C:22][CH3:23].O.C1(C)C=CC(S(O)(=O)=[O:32])=CC=1.C(=O)([O-])O.[Na+]>C(#N)C>[NH2:1][C:2]1[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])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21](=[O:32])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate3×HCID 221733795-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(prop-1-ynyl)pyrazole

Product 1

HCID 186994405-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-propanoylpyrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(prop-1-ynyl)pyrazole (2.1 g) in acetonitrile (40 ml) was added p-toluenesulphonic acid monohydrate (292 g) and the mixture was stirred at room temperature for 1 hour. p-Toluenesulphonic acid monohydrate (1 g) was then added and stirring continued overnight. Acetonitrile (20 ml) was added p-toluenesulphonic acid monohydrate (1 g) were added and stirring continued for 1 hour and then the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution (500 ml) and extracted twice with ether (100 ml). The organic layer was separated, washed with brine (100 ml), dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (70 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a pale brown solid, m.p. 167-169° C.

Workup

  1. stirringstirring continued overnight
  2. additionwere added
  3. stirringstirring
  4. waitcontinued for 1 hour
  5. extractionextracted twice with ether (100 ml)
  6. customThe organic layer was separated
  7. washwashed with brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (70 g)
  11. washeluted with dichloromethane
  12. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-5b1e46d5c9824227a1bba4e7ea7ea062
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

Loading…