Hydrochloric Acid → HCID 10540372, compound

HRID 1464597Notes

Reaction equation

HRID 1464597 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.C(OCC)C.[CH3:20][Si:21]([CH2:24][Mg]Cl)([CH3:23])[CH3:22].Cl>O1CCCC1>[C:9]1([C:7]([OH:8])([CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 27648091-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 178418680HCID 178418680, compound

Product 1

HCID 10540372HCID 10540372, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.505 g (2.7 mmole) of 2-(1H-1,2,4-triazol-1-yl)-acetophenone was added to 50 ml of diethyl ether. The solution was then stirred at room temperature under a stream of nitrogen, and 13.5 ml (13.5 mmole) of a 1 M tetrahydrofuran solution of trimethylsilylmethylmagnesium chloride were added dropwise at such a rate that the temperature of the reaction mixture did not rise higher than 25° C. After the addition was complete, the reaction mixture was stirred for 30 minutes at room temperature; it was then heated under reflux for 6 hours. At the end of this time, the reaction mixture was cooled, and it was then poured into 100 ml of ice-water. Its pH was adjusted to a value of 6 by the addition of 5% w/v aqueous hydrochloric acid, after which it was extracted three times, each time with 50 ml of ethyl acetate. The organic layers were collected, washed three times, each time with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure, to afford a crude oily product. 0.112 g (yield 15%) of the title compound, melting at 86°-87° C., was obtained from this crude oily product by purification through a silica gel chromatography column, eluted with mixtures of ethyl acetate and hexane ranging from 1:1 to 2:1 by volume.

Workup

  1. additionwere added dropwise at such a rate that the temperature of the reaction mixture
  2. customdid not rise higher than 25° C
  3. additionAfter the addition
  4. temperatureit was then heated
  5. temperatureunder reflux for 6 hours
  6. temperatureAt the end of this time, the reaction mixture was cooled
  7. additionIts pH was adjusted to a value of 6 by the addition of 5%
  8. extractionafter which it was extracted three times
  9. customThe organic layers were collected
  10. washwashed three times
  11. dry with materialeach time with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  12. customthe solvent was removed by distillation under reduced pressure
  13. customto afford a crude oily product

Sources & evidence

ORD record
ord-05f37f60800447dc8f03300ed4cfd431
Source dataset
uspto-grants-1994_04
Patent number
US05306712

Reaction notes

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