Dimethyl Sulfate → Methyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 370929Notes

Reaction equation

HRID 370929 reaction equation
Cl(O)(=O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=NC)[C:14]2[N:18]([CH3:19])[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[CH3:25])=[CH:9][CH:8]=1.C(=O)(O)[O-:29].[Na+].S(OC)(OC)(=O)=O.C([O-])(=O)C.[Na+]>CO.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:14]2[N:18]([CH3:19])[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[CH3:25])=[O:29])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 20275539HCID 20275539, compound

Product 1

HCID 618916Methyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetateYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Methyl 5-[(4-chlorophenyl)(methylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate perchlorate (1.5 g, 3.6 mmole) was treated with saturated aqueous sodium bicarbonate and extracted with chloroform (50 ml). The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was treated with dimethyl sulfate (0.62 g, 4.9 mmole) and heated at ~40° C. for one hour. The viscous reaction mixture was dissolved in methanol (10 ml) and treated with sodium acetate (2 g, 24 mmole) and water (2 ml) and heated at reflux overnight. The reaction was cooled and diluted with water (5 ml). The crystalline solid was isolated by filtration, washed with water, air dried, and recrystallized from methanol (10 ml) to yield 0.71 g (65%) of the title compound as a tan solid, m.p. 125°-131° C.

Workup

  1. extractionextracted with chloroform (50 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. temperatureheated at ~40° C. for one hour
  6. temperatureheated
  7. temperatureat reflux overnight
  8. temperatureThe reaction was cooled
  9. customThe crystalline solid was isolated by filtration
  10. washwashed with water, air
  11. customdried
  12. customrecrystallized from methanol (10 ml)

Sources & evidence

ORD record
ord-8a18e981360f43539173f7fbf808cea2
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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