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

HRID 1920263Notes

Reaction equation

HRID 1920263 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 51.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of isoamylnitrite (106.3 g, 0.908 mol) and diiodomethane (1.296 kg, 4.84 mol) in chloroform (500 mL) was heated at 70° C. under a nitrogen atmosphere. A solution of 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile (50.0 g, 0.242 mol) in chloroform (500 mL) was heated to 70° C. was added over a period of 30 minutes while maintaining the reaction temperature at 68° C. to 70° C. during the addition. The reaction was heated for an additional 10 minutes, allowed to cool to room temperature, and concentrated under reduced pressure at 75° C. The residue was purified by column chromatography on silica gel (eluting sequentially with dichloromethane, 1% methanol in dichloromethane, 2% methanol in dichloromethane, and 3% methanol in dichloromethane) to provide 39.4 g (51.3%) of 5-iodo-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile as a tan oil that solidified upon standing.

Workup

  1. additionwas added over a period of 30 minutes
  2. temperaturewhile maintaining the reaction temperature at 68° C. to 70° C.
  3. additionduring the addition
  4. temperatureThe reaction was heated for an additional 10 minutes
  5. concentrationconcentrated under reduced pressure at 75° C
  6. customThe residue was purified by column chromatography on silica gel (
  7. washeluting sequentially with dichloromethane, 1% methanol in dichloromethane, 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-0e764bb1fd0146408094f64e6eca28a2
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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