Potassium Hydroxide → HCID 13424019, compound

HRID 1981067Notes

Reaction equation

HRID 1981067 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][CH2:17][CH:18]([C:19]([O:21]CC)=[O:20])[C:14]2=[C:13]([C:24]([O:26]CC)=[O:25])[C:12]=1[CH3:29])=[O:10].[OH-].[K+]>CO.O>[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][CH2:17][CH:18]([C:19]([OH:21])=[O:20])[C:14]2=[C:13]([C:24]([OH:26])=[O:25])[C:12]=1[CH3:29])=[O:10]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13424018HCID 13424018, compound

Product 1

HCID 13424019HCID 13424019, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Diethyl 5-(1-methyl-5-methylthio-2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylate (25 g) in 200 ml methanol, 50 ml H2O and 25 g KOH were heated to reflux for 8 hours. The resulting mixture was treated with 200 ml of std. NaCl and distilled to remove the methanol. The mixture was acidified with 6N HCl while stirring and then cooled. The crystalline mass obtained was separated by filtration, air dried and recrystallized from ethylacetate-ethanol to yield 21 g of 5-(1-methyl-5 -methylthio-2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo-[1,2-a]-pyrrole-1,7-dicarboxylic acid, m.p. 212°-3° C.

Workup

  1. temperatureto reflux for 8 hours
  2. additionThe resulting mixture was treated with 200 ml of std
  3. distillationNaCl and distilled
  4. customto remove the methanol
  5. temperaturecooled
  6. customThe crystalline mass obtained
  7. customwas separated by filtration, air
  8. customdried
  9. customrecrystallized from ethylacetate-ethanol

Sources & evidence

ORD record
ord-bfb8c40bd6cc4817a53820f703eca990
Source dataset
uspto-grants-1985_04
Patent number
US04511724

Reaction notes

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