Acetic Anhydride → 4-((5-Fluoro-3-pyridinyl)methylene)-2-(2-thienyl)-5(4H)-oxazolone

HRID 1474473

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O.[F:13][C:14]1[CH:15]=[C:16]([CH:20]=O)[CH:17]=[N:18][CH:19]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O>[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:9]2[C:10](=[O:11])[O:12][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:8]2)[CH:17]=[N:18][CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a screw-capped test tube, N-(2-thienylcarbonyl)glycine (56 mg, 0.3 mmol), 5-fluoro-3-pyridinecarboxaldehyde (41 mg, 0.3 mmol), sodium acetate (25 mg, 0.3 mmol) and acetic anhydride (0.3 mL) were added. The test tube was sealed, and it was then stirred at an external temperature of 90° C. Three hours later, the temperature of the reaction solution was returned to room temperature, and water (1.5 mL) was then added thereto. The obtained mixture was stirred at the same temperature as described above for 1.5 hours. Thereafter, the precipitated crystal was collected by filtration, and it was washed with water (5 mL) and was then dried under reduced pressure, so as to obtain 56 mg of the above-captioned compound.

Workup

customThe test tube was sealed
customThree hours
customwas returned to room temperature
stirringThe obtained mixture was stirred at the same temperature
customas described above for 1.5 hours
filtrationThereafter, the precipitated crystal was collected by filtration, and it
washwas washed with water (5 mL)
customwas then dried under reduced pressure

Sources & evidence

ORD record: ord-fae00b65beba4bc18770bfcd40ef8c5d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018238B2

Linked notes

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