ChemicalBook CAS DataBase List 4-Iodo-1-methyl-1H-imidazole

4-Iodo-1-methyl-1H-imidazole synthesis

4synthesis methods

Product Name:4-Iodo-1-methyl-1H-imidazole
CAS Number:71759-87-0
Molecular formula:C4H5IN2
Molecular Weight:208

37067-96-2

71759-87-0

General procedure for the synthesis of 4-iodo-1-methyl-1H-imidazole from 4,5-diiodo-1-methyl-1H-imidazole: At room temperature, EtMgBr (3.0 M ether solution, 11.00 mL, 32.9 mmol) was slowly added dropwise to 4,5-diiodo-1-methyl-1H-imidazole (10.00 g, 29.9 mmol) in anhydrous CH2Cl2 ( 150 mL) solution for more than 15 minutes dropwise. The reaction mixture was then stirred for 20 minutes. After confirming complete consumption of the feedstock by TLC monitoring, the reaction was quenched by adding water (20 mL) to the reaction mixture. The organic and aqueous layers were separated and the aqueous layer was extracted with CH2Cl2 (3 x 50 mL). All organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to afford 4-iodo-1-methylimidazole (15) as a light brown oil (5.86 g, 94% yield).

37067-96-2 Synthesis

37067-96-2
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71759-87-0
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Yield:71759-87-0 94%

Reaction Conditions:

with ethylmagnesium bromide in diethyl ether;dichloromethane at 20; for 0.333333 h;

Steps:

4.1. 4-Iodo-1-methyl-1H-imidazole (15)
EtMgBr (3.0 M solution in ether, 11.00 mL, 32.9 mmol) wasadded to a solution of 14 (10.00 g, 29.9 mmol) in dry CH₂Cl₂(150 mL) at rt. over 15 min. The resulting mixture was stirredfor 20 min and water (20 mL) was added to the reaction mixtureafter running a TLC experiment to confirm all the starting materialis consumed. Then, the layers were separated. The aqueous layerwas extracted with CH₂Cl₂ (3 50 mL) and the combined organiclayers were dried (Na₂SO₄) and concentrated to isolate 15 as paleyellow oil (5.86 g, 94%).

References:

Koswatta, Panduka B.;Kasiri, Sabha;Das, Jayanta K.;Bhan, Arunoday;Lima, Heather M.;Garcia-Barboza, Beatriz;Khatibi, Nicole N.;Yousufuddin, Muhammed;Mandal, Subhrangsu S.;Lovely, Carl J. [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 5,p. 1608 - 1621]

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71759-89-2 Synthesis