2-(Chloromethyl)aniline--hydrogen chloride (1/1) → HCID 15027412, compound

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Reaction Steps

To a suspension of 1.5 g (purity 75%, 7.3 mmol) of 2-mercapto-4,5,6,7-tetrahydro-1H-benzimidazole in 15 ml of ethanol was added 1.3 g (7.3 mmol) of 2-aminobenzyl chloride hydrochloride, and the mixture was stirred for 2 hrs. at room temperature. Ethanol was distilled off under reduced pressure at room temperature. The residue was made alkaline by addition of saturated aqueous sodium hydrogencarbonate and then extracted with 40 ml of chloroform. The chloroform portion was washed with 10 ml of 0.2N NaOH and then with saturated aqueous sodium chloride. The washed chloroform portion was dried over anhydrous sodium sulfate and placed under reduced pressure to distill off the solvent. The residue was purified by silica gel column chromatography using chloroform-methanol to give 1.35 g of the desired compound as a pale yellow oil, yield 71.4%.

Provenance & Evidence