Hydrochloric Acid → HCID 13579306, compound

HRID 1589095Notes

Reaction equation

HRID 1589095 reaction equation
[Na].[C:2](OCC)(=[O:6])[C@H:3]([CH3:5])[OH:4].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([CH2:18][C:19]#[N:20])[CH:15]=[CH:16][CH:17]=1.Cl>C(O)C.O>[CH3:5][CH:3]1[C:2](=[O:6])[C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:21])([F:22])[F:10])[CH:13]=2)=[C:19]([NH2:20])[O:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75360m-TrifluoromethylphenylacetonitrileHCID 92831(L)-ethyl lactateHCID 5360545Sodium

Product 1

HCID 13579306HCID 13579306, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A dry, 500-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was charged with 100 ml of ethanol. To the stirred solvent were added 3.5 g of sodium. After all the metal had dissolved, a solution of 13.0 g of ethyl L-(+)-lactate and 18.5 g of m-trifluoromethylphenylacetonitrile in 30 ml of ethanol was added dropwise to the reaction mixture. The mixture became a deep red and after the addition was complete, the mixture was heated at reflux overnight (about 18 hours). The mixture was then cooled to room temperature and added to 300 ml of water and the resulting mixture was acidified (pH about 1) with 10% hydrochloric acid. The mixture was then extracted with ether (three times) and the organic extracts were washed (two times) with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield a thick oil. This oil was taken up in a mixture of ether/petroleum ether and the desired compound crystallized as a yellow powder. Two crops of crystals were collected to afford a total of 4.7 g of the title compound.

Workup

  1. customA dry, 500-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser
  2. dissolutionAfter all the metal had dissolved
  3. additionafter the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux overnight (about 18 hours)
  6. extractionThe mixture was then extracted with ether (three times)
  7. washthe organic extracts were washed (two times) with saturated aqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a thick oil
  11. customthe desired compound crystallized as a yellow powder
  12. customTwo crops of crystals were collected

Sources & evidence

ORD record
ord-40b7fdf996404f1ca1a851682ee11487
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

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