Hydrochloric Acid → HCID 69693481, compound

HRID 583759Notes

Reaction equation

HRID 583759 reaction equation
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH3:13][N:14]1[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[C:15]1[C:22]([OH:24])=[O:23].[CH2:25](O)[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1.Cl>CN(C)C=O.O>[O:31]1[C:32]2[CH:33]=[CH:34][C:26]([CH:25]([O:23][C:22]([C:15]3[N:14]([CH3:13])[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=3)=[O:24])[C:12]3[CH:11]=[CH:27][C:28]4[O:29][CH2:30][O:31][C:32]=4[CH:33]=3)=[CH:27][C:28]=2[O:29][CH2:30]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10322Piperonyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 222803241-Methyl-1H-pyrrole-2,4-dicarboxylic acid

Product 1

HCID 69693481HCID 69693481, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1,1′-Carbonyldiimidazole (1.3 g, 8.0 mmol) was added to a stirred solution of N-methyl-2,4-pyrrole-dicarboxylic acid (0.6 g, 3.5 mmol) in dimethylformamide (6 mL) under an inert atmosphere and heated to 40° C. After 30 minutes the mixture was allowed to cool, and piperonyl alcohol (1.1 g, 7.1 mmol) was added. The mixture was heated to 60° C. for 3 hours, then poured into water (100 mL), stirred, and acidified with 4N HCl. The resulting mixture was extracted twice with ethyl acetate (60 mL), and the combined extracts were washed successively with water, 0.5 M aqueous sodium bicarbonate, and saturated brine, then dried over MgSO4. The solvent was removed under reduced pressure, and the residue was dissolved in a minimum of hot acetonitrile, cooled, and filtered. The filtrate was taken to dryness under reduced pressure, and the residual product (0.9 g) was chromatographed on a column of silica gel under nitrogen pressure, eluting with ethyl acetate/petroleum ether 2:3. Evaporation of the appropriate fractions and drying afforded 1-methyl-1H-pyrrole-2,4-dicarboxylic acid di-1,3-benzodioxol-5-ylmethyl ester; mp 103-110° C.

Workup

  1. temperatureto cool
  2. temperatureThe mixture was heated to 60° C. for 3 hours
  3. extractionThe resulting mixture was extracted twice with ethyl acetate (60 mL)
  4. washthe combined extracts were washed successively with water, 0.5 M aqueous sodium bicarbonate, and saturated brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in a minimum of hot acetonitrile
  8. temperaturecooled
  9. filtrationfiltered
  10. customthe residual product (0.9 g) was chromatographed on a column of silica gel under nitrogen pressure
  11. washeluting with ethyl acetate/petroleum ether 2:3
  12. customEvaporation of the appropriate fractions
  13. customdrying

Sources & evidence

ORD record
ord-bd4ac510abb44d56aab32ad7933ca434
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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