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]Participants
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
- stirringstirred for 1 h at 0° C. and 3 h at room temperature
- filtrationAfter filtration
- customthe filtrate was evaporated under reduced pressure
- customto remove the solvent
- customThe oily residue thus obtained
- washthe organic layer was washed with brine
- dry with materialdried on anhydrous MgSO4
- filtrationfiltered
- customthe solvent evaporated
- washeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-acetoxybenzoate (5)
- customwas obtained (410 mg, 47% yield)
Sources & evidence
- ORD record
- ord-bc49c70413f04fe580fe4a1df29a9023
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314140B2
Linked notes
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