Aspirin → 4-Isothiocyanatophenyl 2-acetoxybenzoate

HRID 44171

Reaction equation

[CH3:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:3].O[C:15]1[C:23]2N=N[NH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C=CC(C2S[S:49][C:48](=S)C=2)=CC=1>CN(C)C=O.C(OCC)(=O)C>[C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][C:16]1[CH:17]=[CH:18][C:19]([N:20]=[C:48]=[S:49])=[CH:23][CH:15]=1)=[O:12])(=[O:3])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 1 (aspirin, 1200 mg, 6.67 mmol) in 60 mL of dimethylformamide, hydroxybenzotriazole (992 mg, 7.34 mmol) and DCC (1520 mg, 7.34 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 1109 mg, 7.34 mmol) was added and stirred for 1 h at 0° C. and 2 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 ethyl acetate and the precipitate was removed. The solvent was evaporated and the crude product was loaded on a silica gel open column and eluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3) was obtained (150 mg, 7% yield).

Workup

stirringstirred for 1 h at 0° C. and 2 h at room temperature
filtrationAfter filtration
customthe filtrate was evaporated under reduced pressure
customto remove the solvent
customThe oily residue thus obtained
customthe precipitate was removed
customThe solvent was evaporated
washeluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3)
customwas obtained (150 mg, 7% yield)

Sources & evidence

ORD record: ord-7f65cfde5e3e4cd1be0d862d3f8b9bd1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541398B2

Linked notes

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