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

HRID 522833Notes

Reaction equation

I[CH2:2][I:3].[NH2:4][C:5]1[N:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])[C:8]([CH2:15][O:16][CH2:17][CH3:18])=[N:7][C:6]=1C#N.N(OCCC(C)C)=O>C(Cl)(Cl)Cl>[CH2:17]([O:16][CH2:15][C:8]1[N:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])[C:2]([I:3])=[C:6]([C:5]#[N:4])[N:7]=1)[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

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+).

Workup

temperatureAfter cooling to room temperature the mixture
concentrationwas concentrated in vacuo
custompurified by flash chromatography (silica gel, 20% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-108ed5a3fe524c238503ff8ff7f33667
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334268B2

Reaction notes

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