Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

HRID 340668Notes

Reaction equation

HRID 340668 reaction equation
O[C:2]1[C:10]([NH:11][C:12](=[O:23])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[CH2:5][CH2:6]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:17]1([CH2:16][CH2:15][CH2:14][CH2:13][C:12]2[O:23][C:2]3[C:3]4[C:4](=[O:24])[CH2:5][CH2:6][C:7]=4[CH:8]=[CH:9][C:10]=3[N:11]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57781279N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamide

Product 1

HCID 577812092-(4-Phenylbutyl)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneYield 64%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)-5-phenylpentanamide (205 mg, 0.634 mmol) and pyridinium p-toluenesulfonate (31.9 mg, 0.127 mmol) were heated under reflux in xylene (6 mL) for 3 hr. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (124 mg, yield 64%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-4728cbd88fab4fa8887192cb591ee47b
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

Loading…