Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7].[N:13]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:22][C:23]([SH:26])([CH3:25])[CH3:24]>O>[C:23]([S:26][N:13]=[N:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7])([CH3:25])([CH3:24])[CH3:22]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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