Hydrochloric Acid → 3-(Tert-butylthio)diazenyl-4-methylbenzoic acid

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Reaction Steps

To a stirred solution of aqueous HCl (15 mL of concentrated HCl and 50 mL of water) is added 3-amino-4-methyl benzoic acid (5.0 g, 33 mmol). The mixture is cooled in an acetone-ice water bath, followed by the slow addition of a solution of sodium nitrite (2.28 g, 33 mmol) in water (12 mL). The mixture is allowed to stir for 10 min at which point the mixture becomes homogeneous. A saturated aqueous solution of sodium acetate is added until pH˜6. 2-Methylpropane-2-thiol (1.8 mL, 16 mmol) is added and the mixture is stirred for 1 h. The resulting precipitate is collected by filtration, washed with water and dried in vacuo to give 3.85 g (96%) of 3-(tert-butylthio)diazenyl-4-methylbenzoic acid as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 13.2, 7.8, 7.5, 7.3, 2.1, 1.6.

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