Methyl iodide → HCID 22906419, compound

HRID 1379814Notes

Reaction equation

HRID 1379814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]=2[CH3:17])=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].[CH3:24]I>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH3:17])=[C:10]([C:13]([F:14])([F:16])[F:15])[N:11]([CH3:18])[N:12]=2)=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:24])[N:11]=[C:10]([C:13]([F:14])([F:16])[F:15])[C:9]=2[CH3:17])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178427874HCID 178427874, compound

Product 2

HCID 22906419HCID 22906419, compoundHCID 22906427HCID 22906427, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.7 g of 5-(4-chlorophenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazole in 40 mL of acetone was added 5.9 g of potassium carbonate and 1.8 mL of methyl iodide. The mixture was allowed stir overnight at room temperature, filtered and concd in vacuo to give a white solid. This mixture of two isomeric pyrazoles was purified by chromatography on silica (5% ethyl acetate in hexanes) to give 1.8 g (high Rf) of 3-(4-chlorophenyl)-1,4-dimethyl-5-(trifluoromethyl)pyrazole and 2.15 g (low Rf) of 5-(4-chlorophenyl)-1,4-dimethyl-3-(trifluoromethyl)pyrazole. The low Rf material was distilled bulb to bulb (0.1 torr) to give a white, crystalline solid: mp 52°-54° C.; 1HNMR (CDCl3) δ 2.06 (q, 3H, J=1.0 Hz), 3.77 (s, 3H), 7.26 (d, 2H, J=8.5 Hz), 7.50 (d, 2H, J=8.4 Hz); 19FNMR (CDCl3) δ -61.6 (3F). Anal. Calcd for C12H10N2F3Cl1 : C, 52.47; H, 3.677 N, 10.20. Pound: C, 52.517 H, 3.70; N, 10.18.

Workup

  1. filtrationfiltered
  2. customto give a white solid
  3. customwas purified by chromatography on silica (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-11b2e2974ce74d0dbd9f51eb63671cf0
Source dataset
uspto-grants-1997_09
Patent number
US05672715

Reaction notes

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