Diethyl Ether → HCID 9847993, compound

HRID 568200Notes

Reaction equation

HRID 568200 reaction equation
[C:1]([C:3]1[C:7]([S:8][C:9]([F:12])([F:11])[F:10])=[C:6](C=O)[N:5]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:4]=1)#[N:2].[CH3:27][O:28][CH:29](OC)[O:30][CH3:31].C(OCC)C>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:3]1[C:7]([S:8][C:9]([F:10])([F:12])[F:11])=[C:6]([CH:29]([O:30][CH3:31])[O:28][CH3:27])[N:5]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:23])[F:24])=[CH:17][C:16]=2[Cl:26])[N:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 9005Trimethyl orthoformateHCID 118120983-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-formyl-4-trifluoromethylthiopyrazole

Product 1

HCID 9847993HCID 9847993, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolvent

Procedure

The product of Example 3 (2.0 g, 0.005 mol) was combined with trimethylorthoformate (10 ml, 0.09 mol) and para-toluenesulfonic acid monohydrate (50 mg, catalytic) in anhydrous methanol. The mixture was refluxed for 72 hours, cooled to room temperature, poured into diethyl ether, washed with a 1:1 mixture of 10% aqueous sodium hydroxide solution and concentrated aqueous sodium chloride solution (100 ml), water (100 ml) and saturated aqueous sodium chloride solution (100 ml). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to leave an oil that was purified by silica gel chromatography using a 3:1 hexane:dichloromethane solvent mixture. This provided the title compound as a white solid (1.83 g), m.p. about 93° C. Also prepared by this method: Compound 18.

Workup

  1. temperatureThe mixture was refluxed for 72 hours
  2. washwashed with a 1:1 mixture of 10% aqueous sodium hydroxide solution and concentrated aqueous sodium chloride solution (100 ml), water (100 ml) and saturated aqueous sodium chloride solution (100 ml)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto leave an oil that
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-72ab000862d545d49a6bc9a87508e243
Source dataset
uspto-grants-2001_01
Patent number
US06180798B2

Reaction notes

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