Hydrochloric Acid → HCID 22618361, compound

HRID 842167Notes

Reaction equation

HRID 842167 reaction equation
[CH3:1][Mg]I.[Cl:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[C:6]=1[N:16]1[CH:20]=C(C#N)[C:18]([C:23]([F:26])([F:25])[F:24])=[N:17]1.Cl.C([O:30][CH2:31][CH3:32])C>>[C:31]([C:32]1[C:18]([C:23]([F:26])([F:24])[F:25])=[N:17][N:16]([C:6]2[C:7]([Cl:15])=[CH:8][C:9]([C:11]([F:13])([F:14])[F:12])=[CH:10][C:5]=2[Cl:4])[CH:20]=1)(=[O:30])[CH3:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 14280195HCID 14280195, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 22618361HCID 22618361, compound

Procedure

A solution of methylmagnesium iodide (prepared from magnesium (0.26 g) and methyl iodide (1.5 g) in diethyl ether (25 ml)), was treated with a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyano-3-trifluoromethylpyrazole (2 g) in diethyl ether (20 ml), dropwise. The resulting pale yellow solution was refluxed for 24 hours, cooled, and treated with hydrochloric acid (2N, 10 ml). After stirring for 0.5 hour at room temperature, the reaction mixture was diluted with ether (50 ml). The ethereal extract was washed with water (50 ml), dried over anhydrous magnesium sulphate, and evaporated in vacuo to give a yellow gum. This was purified by chromatography on silica (Merck, 230-400 mesh, 0.7 kg cm−2) eluting with a mixture of dichloromethane and petroleum ether (4:1) to give 4-acetyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole as a white solid, m.p. 134° C.

Workup

  1. temperatureThe resulting pale yellow solution was refluxed for 24 hours
  2. temperaturecooled
  3. extractionThe ethereal extract
  4. washwas washed with water (50 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a yellow gum
  8. customThis was purified by chromatography on silica (Merck, 230-400 mesh, 0.7 kg cm−2)
  9. washeluting with a mixture of dichloromethane and petroleum ether (4:1)

Sources & evidence

ORD record
ord-9a2d654fccd944b5b98f06b29dbef621
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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