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With bromine; sodium hydrogencarbonate; In chloroform; water;
Step 1: Synthesis of 2-amino-5-bromo-4-methylthiazole A solution of bromine in chloroform, consisting of 66.7 ml (1.30 mol) of Br2 in 1000 ml of CHCl3, is added dropwise to a solution of 120 g (1.05 mol) of 2-amino-4-methylthiazole in 2300 ml of CHCl3, with stirring. A precipitate appears during the addition. Stirring is maintained for 48 h. The reaction medium is then filtered and the hydrobromide is washed with methylene chloride and then with pentane. The hydrobromide is dissolved in 2000 ml of water and then rendered basic by the addition of 850 ml of a 10percent aqueous solution of sodium bicarbonate. This solution is then extracted with methylene chloride. The organic phase is dried over sodium sulfate. A crystalline residue is obtained after removal of the solvent under vacuum. Brown crystals: m=155 g (crude yield: 76percent) M.p.KB =112°-113° C. 1 H NMR (delta ppm, DMSO) 2.05 (s, 3H, CH3); 7.15 (s, 2H, NH2).
With bromine; In aq. sulfuric acid;
i) 5-Bromo-4-methyl-thiazol-2-ylamine 4-Methyl-thiazol-2-ylamine (4.00 g, 35.0 mmol) was dissolved in 17.5 mL of 20percent aq. sulfuric acid, cooled to 0° C., and treated drop wise with Br2 (1.97 mL, 1.1 eq.). After 10 Min. at 0° C. and 60 Min. at RT, the reaction mixture was carefully poured onto crashed ice/Na2CO3, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Thereby, 5.20 g of the title compound was isolated as light brown solid, sufficiently pure to be used for the next step. MS (ISP): 193.1, 195.1 [M+H]+.
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