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

HRID 1920262Notes

Reaction equation

HRID 1920262 reaction equation
C(ON=O)CC(C)C.I[CH2:10][I:11].[NH2:12][C:13]1[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:16]([CH2:22][CH2:23][CH3:24])=[N:15][C:14]=1C#N>C(Cl)(Cl)Cl>[I:11][C:10]1[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:16]([CH2:22][CH2:23][CH3:24])=[N:15][C:14]=1[C:13]#[N:12]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 585001355-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

Product 1

HCID 585001345-iodo-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of isoamylnitrite (6.1 mL, 45 mmol) and diiodomethane (20 mL) was heated at 85° C. under a nitrogen atmosphere. A solution of 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile (2.50 g, 12.1 mmol) in chloroform (60 mL) was added over a period of 30 minutes. The temperature reached 70° C. during the addition. The reaction was heated for an additional 15 minutes, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was purified by suction filter chromatography on silica gel (eluting with a gradient of 10% to 25% ethyl acetate in hexane) to provide 2.88 g (75%) of 5-iodo-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile as an orange oil that crystallized upon standing.

Workup

  1. additionThe temperature reached 70° C. during the addition
  2. temperatureThe reaction was heated for an additional 15 minutes
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by suction
  5. filtrationfilter chromatography on silica gel (
  6. washeluting with a gradient of 10% to 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8c0043c3270848b99d02c4ffe5ab2510
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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