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ChemicalBook CAS DataBase List Thiazole, 2-iodo-4-Methyl-

Thiazole, 2-iodo-4-Methyl- synthesis

1synthesis methods
-

Yield: 83%

Reaction Conditions:

Stage #1:4-Methylthiazole with butyl magnesium bromide;diisopropylamine in tetrahydrofuran at 20;
Stage #2: with iodine in tetrahydrofuran for 1 h;
Stage #3: with water;sodium thiosulfate in tetrahydrofuran

Steps:

2.a
a) 2-Iodo-4-methyl-thiazole; To a solution of 21.7 mmol diisopropylamine in 50 ml tetrahydrofuran was added dropwise 19.7 mmol butylmagnesium chloride solution (2 M in tetrahydrofuran) and the mixture was stirred at room temperature overnight. 10.1 mmol 4-methylthiazole was then added and stirring continued for 1 hour at room temperature. Finally, a solution of 25.7 mol iodine in 50 ml tetrahydrofuran was added dropwise and stirring continued for a further 1 h. The reaction mixture was then quenched by addition of 20% aqueous sodium thiosulphate solution and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Chromatography (SiO2, ether/heptane) afforded the title compound as a brown solid (yield 83%). MS (m/e): 226.1 (M+H 100%).

References:

F. HOFFMANN-LA ROCHE AG WO2006/72436, 2006, A1 Location in patent:Page/Page column 34

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