Trifluoroacetic acid → 2-Methyl-4-o-tolyl-thiazol-5-ylamine

Participants

Reaction Steps

A solution of (2-methyl-4-o-tolyl-thiazol-5-yl)-carbamic acid tert-butyl ester (340 mg, 1.12 mmol, 1.0 equiv) in dichloromethane (10 mL) was treated with trifluoroacetic acid (0.7 mL, 9.00 mmol, 8.0 equiv) for 24 hours at ambient temperature. The mixture was concentrated under vacuum and the resultant residue dissolved in dichloromethane and washed sequentially with 10% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The collected organic was dried over magnesium sulfate and filtered. The filtrate was passed through an Isolute® SCX-2 cartridge (eluting with dichloromethane, dichloromethane/methanol (1:1) and 2M ammonia in methanol) to afford 62.0 mg (27%) of 2-methyl-4-o-tolyl-thiazol-5-ylamine as a brown residue. LCMS (ESI) m+H=205.0; 1H NMR (400 MHz, CDCl3) δ: 7.33-7.18 (m, 4H), 3.54-3.45 (br, 2H), 2.58 (s, 3H), 2.29 (s, 3H).

Provenance & Evidence