Hydrochloric Acid → HCID 21188104, compound

HRID 1383597Notes

Reaction equation

HRID 1383597 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[CH:8]=1.[N:22]12[CH2:32]CCN=C1CCCCC2.[ClH:33]>CS(C)=O>[Cl:33][C:8]1[N:7]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:6]=[C:5]([C:32]#[N:22])[C:4]=1[C:3]#[CH:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86757110HCID 86757110, compound

Product 1

HCID 21188104HCID 21188104, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of 5-chloro-3-cyano-)-4-(2,2-dibromoethenyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (2.12 g) in dimethylsulphoxide (8 ml) at 15° C. was added dropwise a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.21 ml) in dimethylsulphoxide (7.9 ml). After two hours the reaction mixture was neutralism with 0.5N hydrochloric acid and partitioned between water and dichloromethane. The aqueous layer was thrice extracted with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The aqueous layer was thrice extracted with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with hexane dichloromethane (1:1). Combination and evaporation of suitable fractions followed by recrystallisation from hexane gave the title compound as a light pink solid, m.p. 109.1-109.9° C.

Workup

  1. custompartitioned between water and dichloromethane
  2. extractionThe aqueous layer was thrice extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. extractionThe aqueous layer was thrice extracted with dichloromethane
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluted with hexane dichloromethane (1:1)
  12. customCombination and evaporation of suitable fractions
  13. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-586d5b3ec24b46eaa1f4816f80a951fd
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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