Ammonia → HCID 178498880, compound

HRID 1409431Notes

Reaction equation

HRID 1409431 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.[C:10](O)(=O)[CH:11](C)[CH3:12].N>OS(O)(=O)=O.[N+]([O-])([O-])=O.[Ag+]>[CH:11]([C:2]1[NH:1][CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=1)([CH3:12])[CH3:10]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6590Isobutyric AcidHCID 178418785HCID 178418785, compound

Product 1

HCID 178498880HCID 178498880, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 1118Sulfuric AcidSolvent

Procedure

A solution of methyl 1H-imidazole-4-carboxylate (5.0 g, 39.68 mmol), AgNO3 (4.0 g, 23.81 mmol), isobutyric acid (10.4 g, 119.1 mmol) in 10% H2SO4 (150 ml) was heated at 80° C. for 15 min. An aqueous solution of (NH4)2S2O8 (28.0 g, 119.1 mmol) was added to the mixture dropwise in 15 min at 80° C. The reaction mixture was cooled to RT and poured into ice. The mixture was basified with aqueous ammonia (pH 9) and extracted with EtOAc (500 ml). The organic layer was concentrated and the residue was purified by flash chromatography. Yield 1.5 g. 1H-NMR (400 MHz; CDCl3): δ 1.36 (d, 6H), 3.05-3.14 (m, 1H), 3.87 (s, 3H), 7.62 (s, 1H).

Workup

  1. additionpoured into ice
  2. extractionextracted with EtOAc (500 ml)
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a82b9d0e5f014cec9f6837168066759f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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