Sodium Iodide → HCID 68512261, compound

HRID 1877152Notes

Reaction equation

HRID 1877152 reaction equation
Cl[CH:2]([C:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)[O:10][C:11]=1[CH3:12])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CN(C)C(=O)C.O>[CH3:18][N:16]1[CH:17]=[C:13]([C:9]2[O:10][C:11]([CH3:12])=[C:7]([CH:2]([NH:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[CH2:3][CH:4]([CH3:6])[CH3:5])[CH:8]=2)[CH:14]=[N:15]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12082Methyl 4-aminobenzoateHCID 68509917HCID 68509917, compound

Product 1

HCID 68512261HCID 68512261, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[4-(1-chloro-3-methylbutyl)-5-methylfuran-2-yl]-1-methyl-1H-pyrazole (1.0 g), methyl 4-aminobenzoate (0.9 g), sodium carbonate (0.6 g) and sodium iodide (1.1 g) in N,N-dimethylacetamide (20 mL) was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in methanol (5 mL) and tetrahydrofuran (5 mL), 2N lithium hydroxide (4 mL) was added, and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 55% ethyl acetate/hexane) to give the title compound (0.5 g, 39%) as an amorphous compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (5 mL)
  6. additiontetrahydrofuran (5 mL), 2N lithium hydroxide (4 mL) was added
  7. stirringthe mixture was stirred at 80° C. for 4 hr
  8. additionThe reaction mixture was poured into water
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 55% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5b142e15036748f993fcb0551be82fd9
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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