Diiodomethane → 5-Iodo-1-isopropyl-1H-pyrazole-4-carbonitrile

HRID 886016Notes

Reaction equation

HRID 886016 reaction equation
N(OCCCCC)=O.N[C:10]1[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[CH:12][C:11]=1[C:18]#[N:19].[I:20]CI>>[I:20][C:10]1[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[CH:12][C:11]=1[C:18]#[N:19]

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 10026Pentyl nitriteHCID 179620285-amino-1-isopropyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 582048415-Iodo-1-isopropyl-1H-pyrazole-4-carbonitrile

Procedure

Amyl nitrite (13.00 g, 111.0 mmol) was added to a suspension of 5-amino-1-isopropyl-1H-pyrazole-4-carbonitrile (1.77 g, 11.8 mmol) in Diiodomethane (56.0 mL, 695 mmol) at −10° C. in 30 min. The mixture was stirred for 30 min at room temperature and then heated at 100° C. for 2 hours. The mixture was then cooled and concentrated in high vacuum to give a residue which was partitioned between ethyl acetate and 5% Na2S2O5. The organic layer was washed with water, 0.1% of aq HCl, water, brine, dried and concentrated in vacuum. The residue was purified on silica column eluting with 20-30% ethyl acetate in heptane. Yield 1.68 g (55%). MS (ESI+): 262.2

Workup

  1. temperatureheated at 100° C. for 2 hours
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated in high vacuum
  4. customto give a residue which
  5. customwas partitioned between ethyl acetate and 5% Na2S2O5
  6. washThe organic layer was washed with water, 0.1% of aq HCl, water, brine
  7. customdried
  8. concentrationconcentrated in vacuum
  9. customThe residue was purified on silica column
  10. washeluting with 20-30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-659c8c4354f84c23a51c82fc59f95d00
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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