2-Amino-6-ethoxybenzothiazole synthesis
- Product Name:2-Amino-6-ethoxybenzothiazole
- CAS Number:94-45-1
- Molecular formula:C9H10N2OS
- Molecular Weight:194.25
Yield: 74%
Reaction Conditions:
Stage #1:potassium thioacyanate;4-Ethoxyaniline with bromine;acetic acid at 20;Cooling with ice;
Stage #2: with ammonium hydroxide in water; pH=11
Steps:
5.1.2. General synthetic procedure for 2-amino-6-Substituted benzothiazoles (3a-k)
General procedure: A mixture of 0.1 mol of 4-substituted aniline and 0.1 mol of Potassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled in an ice bath and stirred for 10-20 min, and then 0.1 mol bromine in glacial acetic acid was added dropwise at such a rate to keep the temperature below 10 °C throughout the addition. The reaction mixture was stirred at room temperature for 2-4 h, the hydrobromide (HBr) salt thus separated out was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH4OH) and the resulting precipitate was filtered, washed with water and dried to get the desired product 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
References:
Patel, Rahul V.;Patel, Paresh K.;Kumari, Premlata;Rajani, Dhanji P.;Chikhalia, Kishor H. [European Journal of Medicinal Chemistry,2012,vol. 53,p. 41 - 51] Location in patent:experimental part
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