Water → Zomepirac Sodium

HRID 370930Notes

Reaction equation

HRID 370930 reaction equation
Cl(O)(=O)(=O)=[O:2].[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]C)=[O:22])=[CH:16][C:15]=2[CH3:25])=[CH:9][CH:8]=1.S(OC)(OC)(=O)=[O:29].C(=O)(O)[O-].[Na+:39].O>C(Cl)(Cl)Cl.CO>[OH2:2].[OH2:22].[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])=[O:22])=[CH:16][C:15]=2[CH3:25])=[O:29])=[CH:9][CH:8]=1.[Na+:39]

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 20275539HCID 20275539, compound

Product 1

HCID 23663418Zomepirac SodiumYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Methyl 5-[(4-chlorophenyl)(methylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate perchlorate (1.5 g, 3.6 mmole) was dissolved in chloroform, extracted with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated. The residue was treated with dimethyl sulfate (0.5 g, 3.9 mmole) and allowed to stand at 18°-30° C. for two hours. The reaction was dissolved in methanol (10 ml) and treated with saturated aqueous sodium bicarbonate (5 ml) and water (2 ml). The solution was heated at reflux overnight, then allowed to cool to room temperature. The solid was isolated by filtration, washed with water, and air dried to yield 0.95 g (76%) of the title compound as a light tan solid, m.p. >230° C.

Workup

  1. extractionextracted with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. temperatureThe solution was heated
  5. temperatureat reflux overnight
  6. customThe solid was isolated by filtration
  7. washwashed with water, and air
  8. customdried

Sources & evidence

ORD record
ord-71584cf4f66f47c9897f3864fc5e15e4
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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