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ChemicalBook CAS DataBase List 4,5-Diiodo-2-methyl-1H-imidazole

4,5-Diiodo-2-methyl-1H-imidazole synthesis

3synthesis methods
-

Yield: 100%

Reaction Conditions:

with iodine;sodium carbonate in 1,4-dioxane;water at 20; for 24 h;

Steps:

B.1
To a slightly yellow homogeneous solution of 2-methylimidazole (15.000 g; 182.680 mmol) in dioxane (305 ml) and distilled water (305 ml) was added successively, at rt (in one portion), sodium carbonate (58.086 g; 548.040 mmol), and iodine (102.005 g; 401.896 mmol). The resulting brown heterogeneous reaction mixture was further stirred at rt, under nitrogen, for 24h. EA (900 ml) was then added followed by an aq. solution of sodium thiosulfate (54 g Na2S2θ3 in 540 ml of water). The yellow homogeneous organic layer was separated and additionally washed with an aq. solution of sodium thiosulfate (36 g Na2S2O3 in 300 ml of water), and finally with brine (300 ml). The yellow organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give the pure product 4, 5-diiodo-2-methyl-1 /-/-imidazole as a yellow solid which was further dried under HV (61.000 g; 100%). LC-MS: tR = 0.52 min.; [M+H]+ = 335.14 g/mol.

References:

ACTELION PHARMACEUTICALS LTD WO2008/78291, 2008, A1 Location in patent:Page/Page column 62

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