2-Amino-4-methoxybenzothiazole is a useful research intermediate for the synthesis of various benzothiazole and aminobenzothiazoles derivatives with antibacterial and antifungal activity.
An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
ACUTE/CHRONIC HAZARDS: When heated to decomposition 4-Methoxy-2-aminobenzothiazole emits very toxic fumes of NOx and SOx.
Flash point data for 4-Methoxy-2-aminobenzothiazole are not available. 4-Methoxy-2-aminobenzothiazole is probably combustible.
2-Amino-4-methoxybenzothiazole on condensation reaction with 4-acetamidobenzaldehyde affords tridentate Schiff bases. It reacts with 2,4,6-trichloro 1,3,5-triazine to give 2-(4-methoxybenzothiazol-2′-ylamino)-4-(phenylthioureido)-6-(substitutedthioureido)-1,3,5-triazines.
General procedure for the synthesis of 2-amino-4-methoxybenzothiazole from 1-(2-methoxyphenyl)thiourea: 1-(2-methoxyphenyl)thiourea (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To this solution, lithium bromide (2.6 g, 0.03 mol) was added at room temperature, followed by slow dropwise addition of bromine (1 ml, 0.02 mol) under ice bath conditions. The reaction mixture was heated to 40°C and the reaction was stirred at this temperature for 17 hours. After completion of the reaction, the system was cooled to room temperature and allowed to stand for 2 hours. The reaction product was collected by filtration and washed with acetic acid. Finally, the resulting white solid was dried in a vacuum oven to afford the target product 2-amino-4-methoxybenzothiazole (3.5 g, 94.08% yield).
[1] Patent: US2016/102066, 2016, A1. Location in patent: Paragraph 0021; 0025; 0027
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[4] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189
[5] Chem.Abstr., 1941, p. 452
