Sulfuric Acid → N-[2-(2-Methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide

HRID 340703Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[CH:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-[2-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethyl]acetamide (63.5 mg, 0.248 mmol) was dissolved in toluene (2.5 mL), sulfuric acid (24.3 μL, 0.248 mmol) was added, and the mixture was stirred at 100° C. for 5 hr. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (40.0 mg, yield 63%).

Workup

extractionThe mixture was extracted with ethyl acetate
washwashed with saturated brine
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

Sources & evidence

ORD record: ord-3d2c8d98e8b14bfea76a5c2a19aa713d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895591B2

Reaction notes

Loading…