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Aspirin → 4-Carbamoylphenyl 2-acetoxybenzoate

HRID 44164
Notes
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Reaction equation

HRID 44164 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].OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:40]1[CH:48]=[CH:47][C:43]([C:44]([NH2:46])=[O:45])=[CH:42][CH:41]=1>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][C:40]1[CH:48]=[CH:47][C:43]([C:44](=[O:45])[NH2:46])=[CH:42][CH:41]=1)=[O:8])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 2244AspirinHCID 10868DicyclohexylcarbodiimideHCID 650524-HydroxybenzamideHCID 178418300HCID 178418300, compound

Product 1

HCID 593455924-Carbamoylphenyl 2-acetoxybenzoateYield 47%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 1 (acetylsalicylic acid, 500 mg, 2.77 mmol) in 15 mL of dimethylformamide, hydroxybenzotriazole (412 mg, 3.05 mmol) and DCC (628 mg, 3.05 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 418 mg, 3.05 mmol) was added and stirred for 1 h at 0° C. and 3 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in chloroform; the organic layer was washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-acetoxybenzoate (5) was obtained (410 mg, 47% yield).

Workup

  1. stirringstirred for 1 h at 0° C. and 3 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. washthe organic layer was washed with brine
  7. dry with materialdried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-acetoxybenzoate (5)
  11. customwas obtained (410 mg, 47% yield)

Sources & evidence

ORD record
ord-14e2d3bb7a314986a95ee77f3c224d92
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541398B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes