Dimethyl Sulfoxide → HCID 19914734, compound

HRID 1090179Notes

Reaction equation

HRID 1090179 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:23])([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)CO)=[CH:10][CH:9]=1.CS(C)=O.[F:28][C:29]([F:33])=[C:30]([F:32])[F:31].[OH2:34]>C1COCC1.C(O)(C)(C)C>[N:18]1([CH:17]([CH3:1])[C:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)([O:34][C:30]([F:32])([F:31])[CH:29]([F:33])[F:28])[CH3:23])[CH:22]=[N:21][CH:20]=[N:19]1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8301TetrafluoroethyleneHCID 19914729HCID 19914729, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19914734HCID 19914734, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An amount of 6.1 of potassium tert-butoxide is added, under nitrogen atmosphere at -10° C., to 1.9 g of 2-(4-chlorphenyl)-2-methyl-3-(1,2,4-triazol-1-yl)-1-hydroxy-propane dissolved in 6.5 ml of anhydrous THF, 13 ml. of anhydrous DMSO, and 13 ml of anhydrous tert. butanol. The apparatus is then first put under vacuum and tetrafluoroethylene is introduced by maintaining the reaction mass under this gas atmosphere over a time of one night, at room temperature. The reaction mixture then is poured into water, and extracted with ethyl acetate. The extract is washed with water, dried over Na2SO4 and evaporated; the raw product obtained is purified by chromatography over silica gel, using n-hexane-ethyl acetate 1:1 as eluent. 1 g of an oil is isolated having the structure indicated in the title of this example, according to the following spectroscopic data:

Workup

  1. additionis introduced
  2. temperatureby maintaining the reaction mass under this gas atmosphere over a time of one night
  3. customat room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customthe raw product obtained
  9. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-99b1ac773fc94a92978a73b9ebb8f241
Source dataset
uspto-grants-1992_01
Patent number
US05081141

Reaction notes

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