1,2-Dichloroethane → HCID 70972224, compound

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Reaction Steps

DMF (15.9 mL) was added to a round bottom flask containing 3-(oxazol-5-yl)benzoic acid (0.99 gm, 5.23 mmol), methylamine hydrochloride (0.39 gm, 5.76 mmol), EDC (1.10 gm, 5.76 mmol), and HOAt (0.78 gm, 5.76 mmol). DIPEA (2.29 mL, 13.08 mmol) was then added. The reaction mixture was stirred at rt overnight. After 24 h the mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes then 15% MeOH in EtOAc to give the product, N-methyl-3-(oxazol-5-yl)benzamide, (0.50 gm, 2.49 mmol, 48% yield) as a white solid. Anal. Calcd. for C11H10N2O2 m/z 202.1, found: 203.1 (M+H)+.

Provenance & Evidence