Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-Fluoro-4-(5-(phenylthio)benzo[d]oxazol-2-yl)benzaldehyde

HRID 2075265Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-fluoro-4-formyl-N-(2-hydroxy-5-(phenylthio)phenyl)benzamide (0.180 g, 0.490 mmol) and pyridinium p-toluenesulfonate (0.123 g, 0.490 mmol) in 5.0 mL toluene was heated to 130° C. in a sealed tube for a total of 6 h. The reaction was cooled and was partitioned between 1N NaOH and EtOAc. The organic layer was washed 1× brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a solid that was purified by silica gel chromatography, 0-30-60% EtOAc/hexanes to give 3-fluoro-4-(5-(phenylthio)benzo[d]oxazol-2-yl)benzaldehyde as a yellow solid. MS (ESI) m/z: Calculated: 349.1; Observed: 350.0 (M++1).

Workup

temperatureThe reaction was cooled
customwas partitioned between 1N NaOH and EtOAc
washThe organic layer was washed 1× brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a solid
customthat was purified by silica gel chromatography, 0-30-60% EtOAc/hexanes

Sources & evidence

ORD record: ord-6c408f585e0144feabe077b46fd0c163
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

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