Aspirin → 2-(Diethylamino)-2-oxoethyl 2-acetoxybenzoate

HRID 1461120Notes

Reaction equation

HRID 1461120 reaction equation
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].Cl[CH2:15][C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17].C(N(CC)CC)C.[I-].[Na+]>C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:15][C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 2244AspirinHCID 5238Sodium IodideHCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamide

Product 1

HCID 156162522-(Diethylamino)-2-oxoethyl 2-acetoxybenzoateYield 70.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of acetylsalicylic acid (5.4 g. 0.03 mole) and 2-chloro-N,N-diethylacetamide (4.5 g, 0.03 mole) in 40 ml of ethyl acetate was added triethylamine (4.2 ml, 0.03 mole) and sodium iodide (0.45 g, 0.003 mole). The mixture was refluxed for 4 h. After cooling the mixture was filtered and the filtrate washed with 2M hydrochloric acid, 5% sodium bicarbonate and water. After drying over anhydrous sodium sulphate the solution was evaporated in vacuo leaving an oil which crystallized by trituration with ethanol. Recrystallization from 80% ethanol afforded 6.2 g (70%) of the title compound. Mp 75°-76° C.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. temperatureAfter cooling the mixture
  3. filtrationwas filtered
  4. washthe filtrate washed with 2M hydrochloric acid, 5% sodium bicarbonate and water
  5. dry with materialAfter drying over anhydrous sodium sulphate the solution
  6. customwas evaporated in vacuo
  7. customleaving an oil which
  8. customcrystallized by trituration with ethanol
  9. customRecrystallization from 80% ethanol

Sources & evidence

ORD record
ord-ec6aa1802f2a4dab91b128aeda412afe
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

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