Hydrochloric Acid → HCID 9803806, compound

HRID 399022Notes

Reaction equation

HRID 399022 reaction equation
[CH3:1][Li].[C:3]([C:5]1[C:9]([S:10][C:11]([F:14])([F:13])[F:12])=[C:8]([CH:15]=[O:16])[N:7]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])[N:6]=1)#[N:4].Cl>C(OCC)C.[Cu]I>[C:3]([C:5]1[C:9]([S:10][C:11]([F:13])([F:12])[F:14])=[C:8]([CH:15]([OH:16])[CH3:1])[N:7]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:26])([F:27])[F:25])=[CH:19][C:18]=2[Cl:28])[N:6]=1)#[N:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 118120983-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-formyl-4-trifluoromethylthiopyrazoleHCID 178418348HCID 178418348, compound

Product 1

HCID 9803806HCID 9803806, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Copper (I) iodide (6.1 g, 0.032 mol) was suspended in anhydrous diethyl ether and cooled to 0° C. Methyllithium (1.6M in diethyl ether, 40 ml, 0.064 mol) was added via cannula and stirred 10 minutes. A solution of the product of Example 3 (10 g, 0.023 mol) in diethyl ether was added via cannula creating a bright yellow suspension. After 15 minutes, 10% aqueous hydrochloric acid (40 ml) was added while venting the reaction vessel. The remaining suspension was filtered through Celite® and washed with diethyl ether several times. The organic phase was washed with saturated sodium hydrogen carbonate solution, saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Trituration from pentane provided crystals that were purified by silica gel chromatography using ethyl acetate:hexanes. The title compound was isolated as a white solid (7.56 g), m.p. about 123° C.

Workup

  1. waitAfter 15 minutes
  2. filtrationThe remaining suspension was filtered through Celite®
  3. washwashed with diethyl ether several times
  4. washThe organic phase was washed with saturated sodium hydrogen carbonate solution, saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customTrituration from pentane provided crystals that were purified by silica gel chromatography

Sources & evidence

ORD record
ord-8d88ffebf38a46a09b989801a235c4f9
Source dataset
uspto-grants-1998_10
Patent number
US05817688

Reaction notes

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