Hydrochloric Acid → HCID 178429419, compound

HRID 1861593Notes

Reaction equation

HRID 1861593 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([O:15]C3N(C)N=C(C(F)(F)F)C=3)[N:9]=2)=[CH:5][C:4]([C:26]([F:29])([F:28])[F:27])=[N:3]1.[OH-].[Na+].Cl>CS(C)=O.O.CCCCC.C(OCC)(=O)C>[OH:15][C:10]1[N:9]=[C:8]([O:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:5]=2)[CH:13]=[C:12]([CH3:14])[CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 154771722,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine

Product 1

HCID 178429419HCID 178429419, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 22335286Ethyl acetate pentaneSolvent

Procedure

A mixture of 2,6-bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine (prepared according to WO 94/22833; 4.2 g, 10 mmol) and NaOH (1 g, 25 mmol) is heated in DMSO (50 ml) and water (5 ml) for 36 h at 100° C. After cooling, the reaction mixture is diluted with water and acidified with hydrochloric acid. The mixture is diluted with pentane/ethyl acetate (300 ml by volume ration 1/1) and the organic layer is washed 6 times with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 8/2 v/v and 7/3 v/v) yields the title compound (1.9 g, 70% yield) of m.p. 159° C.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer is washed 6 times with water
  3. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 8/2 v/v and 7/3 v/v)

Sources & evidence

ORD record
ord-28ef9682a4a44c0b900e0cbabffbf1a3
Source dataset
uspto-grants-2003_03
Patent number
US06534447B1

Reaction notes

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