Water → HCID 57975376, compound

HRID 1865050Notes

Reaction equation

HRID 1865050 reaction equation
C(ON=O)CC(C)C.[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:23])[C:16]([CH3:22])=[C:17]([C:20]#[N:21])[C:18]=1N)=[O:13])[CH3:10].[I:24]CI.O>C(#N)C>[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:23])[C:16]([CH3:22])=[C:17]([C:20]#[N:21])[C:18]=1[I:24])=[O:13])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 57975248HCID 57975248, compound

Product 1

HCID 57975376HCID 57975376, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

Add isoamylnitrite (2.5 Eq.) to 3-amino-4-cyano-1,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in preparation 44) and diiodomethane (3.5 eq.) in acetonitrile (10 mL) with stirring at 55° C. under a nitrogen atmosphere. Slowly heat the reaction mixture to 75° C. and heat at this temperature for 3 hours. Cool to room temperature and pour into water, and extract the quenched reaction with ethyl acetate. Wash the organic extracts with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum. Purify the residue by silica gel chromatography (Prep.2000) eluting with methylene chloride to provide a solid. Recrystallize from ethyl acetate to provide the title compound as crystals. Mass spectrum (m/e): 318.0 M*). (Bruker 300) 1H NMR (CDCl3) 4.31-4.38 (2H, dd), 3.83-3.86 (3H, s), 2.41-2.44 (3H, s), 1.40-1.44 (3H, t).

Workup

  1. temperatureSlowly heat the reaction mixture to 75° C.
  2. temperatureheat at this temperature for 3 hours
  3. temperatureCool to room temperature
  4. extractionextract
  5. customthe quenched reaction with ethyl acetate
  6. washWash the organic extracts with water
  7. dry with materialdry over potassium carbonate
  8. filtrationfilter
  9. concentrationconcentrate under reduced vacuum
  10. customPurify the residue by silica gel chromatography (Prep.2000)
  11. washeluting with methylene chloride
  12. customto provide a solid
  13. customRecrystallize from ethyl acetate

Sources & evidence

ORD record
ord-ae02d43cc559490581f55cc7212aeb5f
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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