Diiodomethane → HCID 58500144, compound

HRID 1920275Notes

Reaction equation

HRID 1920275 reaction equation
C(ON=O)CC(C)C.I[CH2:10][I:11].[NH2:12][C:13]1[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:16]([CH2:27][CH3:28])=[N:15][C:14]=1C#N>C(Cl)(Cl)Cl>[C:13]([C:14]1[N:15]=[C:16]([CH2:27][CH3:28])[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:24])=[O:25])[C:10]=1[I:11])#[N:12]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 58500136HCID 58500136, compound

Product 1

HCID 58500144HCID 58500144, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of isoamylnitrite (0.30 g, 2.6 mmol), diiodomethane (2 mL), and chloroform (3 mL) was heated at 85° C. A mixture of N-[4-(5-amino-4-cyano-2-ethyl-1H-imidazol-1-yl)butyl]methanesulfonamide (0.2 g, 0.7 mmol) and chloroform (8 mL) was added over a period of 15 minutes. The reaction was stirred and heated at 80° C. for an additional 10 minutes, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was purified through a layer of silica gel (15 g, eluting sequentially with chloroform, 2% methanol in chloroform, 4% methanol in chloroform, 8% methanol in chloroform, and 10% methanol in chloroform) to provide 0.16 g (57%) of N-[4-(4-cyano-2-ethyl-5-iodo-1H-imidazol-1-yl)butyl]methanesulfonamide as an amber syrup.

Workup

  1. additionwas added over a period of 15 minutes
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through a layer of silica gel (15 g
  5. washeluting sequentially with chloroform, 2% methanol in chloroform, 4% methanol in chloroform

Sources & evidence

ORD record
ord-71aa10c411ab438f9f95cff31fd5fd01
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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