Sodium Hydroxide → N-(7-fluoro-4-methoxy-1-benzothien-2-yl)-N,N-dimethylamine

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Reaction Conditions

Reaction Steps

A solution of 2-(5-fluoro-2-methoxyphenyl)-2-hydroxy-N,N-dimethylethanethioamide (0.5 g, 2.1 mmol) in Eaton's reagent (5 mL) were combined and heated rapidly to 60° C. 5 and left for 1 h. After cooling to room temperature over 2 hours the mixture was dropwise addition into prechilled aqueous sodium hydroxide (2 N, 16.25 mL) with constant stirring. This solution was then extracted with methyl tert-butyl ether (5×20 mL) and the combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give a yellow solid. This was purified by flash chromatography with a gradient of 0-2% diethyl ether in hexane and gave 0.2 g of yellow solid containing an impurity, this was triturated with hexane to leave a colourless solid (0.155 g, 34%) of the title compound; δH (300 MHz, CDCl3) 6.70-6.52 (2H, m, ArH), 6.12-6.10 (1H, m, ArH) 3.90 (3H, s, OCH3) and 3.2 (6H, s, N(CH3)2), M+H=226.1.

Provenance & Evidence