Hydrochloric Acid → HCID 49782231, compound

HRID 1518905Notes

Reaction equation

HRID 1518905 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[H-].[Na+].[C:13](Cl)(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O1CCCC1>[C:13]([NH:6][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[F:1])(=[O:22])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 660233-Phenylprop-2-enoyl chlorideHCID 679642-Fluorobenzamide

Product 1

HCID 49782231HCID 49782231, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, 2-fluorobenzamide (1.41 g, 10.0 mmol), sodium hydride (60% dispersion in mineral oil, 1.04 g, 25.0 mmol) and tetrahydrofuran (3 mL) were stirred under ice-cooling. A solution of cinnamoyl chloride (1.68 g, 10.0 mmol) in tetrahydrofuran (3 mL) was added thereto, and the mixture was warmed to room temperature. After stirring for 1 hr, to the mixture was added diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogencarbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (1.91 g) as a white solid. The yield was 70%.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-208f46375911432b9316fb165ffcf207
Source dataset
uspto-grants-2015_07
Patent number
US09073823B2

Reaction notes

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