Benzoyl chloride → HCID 22932821, compound

HRID 1727350Notes

Reaction equation

HRID 1727350 reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([NH2:5])=[O:4].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:7]([O:1][CH:2]([CH3:6])[C:3]([NH2:5])=[O:4])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 94220LactamideHCID 516892Sodium Bicarbonate

Product 1

HCID 22932821HCID 22932821, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-hydroxypropionamide (10.8 g, 121 mmol) in pyridine (40 mL) was added benzoyl chloride (14.2 mL, 122 mmol) at 0° C. and the reaction mixture was allowed to warm up to room temperature. The resulting mixture was stirred at room temperature for 3 hours and the solvent was removed under reduced pressure to give a residue. To the residue an aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extracts were washed with an 1N hydrochloric acid twice and brine. The organic solution was dried, and concentrated under reduced pressure. The obtained crude crystal was recrystallized from ethyl acetate-hexane to give a title compound (17.9 g, yield 77%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto give a residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extracts were washed with an 1N hydrochloric acid twice
  5. customThe organic solution was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude crystal
  8. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-908a1e0f4c3c4fffb260f0183e5b2a8b
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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