p-Toluenesulfonic acid → HCID 66621211, compound

HRID 415281Notes

Reaction equation

HRID 415281 reaction equation
O[C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:13]3[O:26][C:2]4[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=4[N:12]=3)=[CH:15][CH:16]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66620758HCID 66620758, compound

Product 1

HCID 66621211HCID 66621211, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 2-hydroxy-3-(4-(pyridin-3-yl)benzamido)benzoate (1.04 g, 3 mmol) and 4-methylbenzenesulfonic acid (1.2 g, 6 mmol) were added to toluene (20 mL) and the mixture was stirred under reflux for 2 days. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 10:1). 150 mg of methyl 2-(4-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained, yield: 15%. 1H-NMR (400 MHz, DMSO-d6) δ 4.02 (s, 3H), 7.55-7.59 (m, 1H), 7.97-7.99 (m, 1H), 8.04-8.06 (d, J=8.0 Hz, 2H), 8.13-8.15 (m, 1H), 8.21-8.24 (m, 1H), 8.33-8.35 (d, J=8.2 Hz, 2H), 8.65-8.66 (m, 1H), 9.03-9.04 (d, J=2.0 Hz, 1H); LC-MS (ESI) m/z: 331 (M+1)+.

Workup

  1. temperatureunder reflux for 2 days
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 10:1)

Sources & evidence

ORD record
ord-6723145ab27445d99eb3edfd16e8045a
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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