Sodium Chloride → HCID 13424022, compound

HRID 1731618Notes

Reaction equation

HRID 1731618 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][CH:4]=[C:3]1[C:9]([C:11]1[N:15]2[CH2:16][CH:17]([C:19]([O:21]CC)=[O:20])[CH2:18][C:14]2=[CH:13][C:12]=1[CH3:24])=[O:10].[Cl-].[Na+]>CO.[OH-].[Na+]>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][CH:4]=[C:3]1[C:9]([C:11]1[N:15]2[CH2:14][CH2:18][CH:17]([C:19]([OH:21])=[O:20])[C:16]2=[CH:24][C:12]=1[CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 54273876HCID 54273876, compound

Product 1

HCID 13424022HCID 13424022, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (±)-ethyl 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-2-carboxylate (0.50 g) in methanol (10 ml) and 10% sodium hydroxide (10 ml) were stirred at room temperature for 2 hours. A saturated sodium chloride solution was added to the solution and the methanol removed under reduced pressure. The aqueous solution was acidified with 3N hydrochloric acid with stirring and cooling and the resulting precipitate collected by filtration. The solids were washed with water, air dried, and recrystallized from ethyl acetate-hexane to give (±)-5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (0.45 g, 98% yield) m.p. 182°-184° C.

Workup

  1. customthe methanol removed under reduced pressure
  2. temperaturecooling
  3. filtrationthe resulting precipitate collected by filtration
  4. washThe solids were washed with water, air
  5. customdried
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-562b75958c25472d8cdc93afbeb37a35
Source dataset
uspto-grants-1986_11
Patent number
US04622407

Reaction notes

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