Benzoyl chloride → HCID 839850, compound

HRID 268306Notes

Reaction equation

HRID 268306 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCCl>[C:7]([N:3]1[CH2:4][CH2:5][O:1][C:2]1=[O:6])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 739492-Oxazolidinone

Product 1

HCID 839850HCID 839850, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-oxazolidinone (4.68 g; 0.05 mol) in 1,2-dichlorethane (60 ml), there is added benzoyl chloride (5.6 ml, 0.05 mol) and triethylamine (7.0 ml; 0.05 mol), with stirring at ambient temperature for 30 mins. The solution is then concentrated at reduced pressure and ethyl acetate is added, thereafter it is filtered to remove the base hydrochloride; the filtrate is partly evaporated and diluted with n-heptane and the precipitated solid is removed by filtration. After washing with water and drying, it gives 3-benzoyl-2-oxazolidinone (5.94 g; 90%). From absolute ethanol it crystallizes in nacar scales with m.p. = 166°-170°C. A portion of the substance in ethanol, with a catalytic amount of sodium ethoxide at room temperature immediately gives ethyl benzoate and, with aniline, benzanilide.

Workup

  1. concentrationThe solution is then concentrated at reduced pressure and ethyl acetate
  2. additionis added
  3. filtrationit is filtered
  4. customto remove the base hydrochloride
  5. customthe filtrate is partly evaporated
  6. additiondiluted with n-heptane
  7. customthe precipitated solid is removed by filtration
  8. washAfter washing with water
  9. customdrying

Sources & evidence

ORD record
ord-ef76ceb82f5f4015a35a21e012c06d74
Source dataset
uspto-grants-1976_03
Patent number
US03947465

Reaction notes

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