Réaction #91979

Équation de réaction

isoamyl nitrite

Diiodomethane

5-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile

→

title compound

Rendement 57.3%

2-(Ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-5-iodo-1H-imidazole-4-carbonitrile

Rendement 57.3%

Solvants

chloroform

chloroform

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature the mixture
2. 2
   Concentrationwas concentrated in vacuo
3. 3
   Autrepurified by flash chromatography (silica gel, 20% to 50% ethyl acetate in heptane)

Mode opératoire

Diiodomethane (14.5 ml, 180 mmol) was added under argon with stirring to a suspension of 5-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile (4.36 g, 18.3 mmol) in chloroform (170 mL). The reaction mixture was heated to 80° C., a solution of isoamyl nitrite (9.86 ml, 73.2 mmol) in chloroform (30 mL) was added with a syringe pump over a period of 40 min and the mixture was stirred for another 30 min at 80° C. After cooling to room temperature the mixture was concentrated in vacuo and purified by flash chromatography (silica gel, 20% to 50% ethyl acetate in heptane) to give the title compound (3.66 g, 57%) as brown oil; LC-MS (UV peak area, ESI) 90%, 350.0374 (MH+).

Source