Dimethyl Sulfoxide → (3-Dimethylaminomethyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

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Reaction Conditions

Reaction Steps

Me3SiBr (0.23 mL, 1.75 mmol, 1.1 equiv) and DMSO (0.12 mL, 1.75 mmol, 1.1 equiv) are added sequentially and dropwise to a cold (−35° C.) solution of 3-thiophenylacetaldehyde (200 mg, 1.59 mmol) in CH3CN (3.0 mL), under an argon atmosphere. The resulting mixture is allowed to warm to 0° C., to stir for 50 min, then to warm to room temperature and to stir for 10 min. CH3CN (5.0 mL) is added to the reaction mixture, followed by addition of (3-dimethylaminomethyl-phenyl)-thiourea (Example 2) (333 mg, 1.59 mmol). The reaction mixture is heated to reflux for 1 h, allowed to cool to RT and concentrated in vacuo. MPLC (CH3CN/H2O/TFA) purification affords the title compound: ES-MS: 316.0 [M+H]+; single peak at tR=3.19 min (System 2).

Provenance & Evidence