Dimethyl Sulfoxide → HCID 19860763, compound

HRID 1165696Notes

Reaction equation

HRID 1165696 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][C:13]1(O)[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[O:14]1.C(=O)([O-])[O-:24].[K+].[K+].CS(C)=O>O>[CH3:12][CH:13]1[CH2:17][C:16]2[CH:18]=[C:19]([O:24][C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=3)[CH:20]=[CH:21][C:15]=2[O:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 19860755HCID 19860755, compound

Product 1

HCID 19860763HCID 19860763, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2.18 grams (0.012 mole) of 2-chloro-5-trifluoromethyl pyridine, 1.80 grams (0.012 mole) of 2,3-dihydro-2-methyl benzofuranol, 2.07 grams (0.015 mole) of potassium carbonate and 80 milliliters of dimethylsulfoxide was heated, under anhydrous conditions, at a temperature in the range of 65°-72° C. for about 72 hours. After heating was discontinued, the mixture was stirred overnight, then poured into 800 milliliters of water and extracted with 2×250 milliliter portions of diethylether. The combined organic extracts were washed with 2×300 milliliter portions of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo affording 2.60 grams of brown oil. The crude product was purified by column chromatography and eluted with 5:95 v/v ethyl acetate:hexane affording 1.64 grams of white crystals confirmed by spectroscopic analysis as the desired product.

Workup

  1. temperaturewas heated, under anhydrous conditions, at a temperature in the range of 65°-72° C. for about 72 hours
  2. temperatureAfter heating
  3. extractionextracted with 2×250 milliliter portions of diethylether
  4. washThe combined organic extracts were washed with 2×300 milliliter portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ba174530e7a44418ca130c190192d79
Source dataset
uspto-grants-1990_03
Patent number
US04911754

Reaction notes

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