Ethylene Glycol → HCID 19095275, compound

HRID 486551Notes

Reaction equation

HRID 486551 reaction equation
[C:1]1([C:7]2[N:8]([CH2:12][CH2:13][NH:14]C(=O)C)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)CO.[OH-].[K+].[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]>O.C(O)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[NH2:14][CH2:13][CH2:12][N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 444972Fumaric AcidHCID 19095354HCID 19095354, compound

Product 1

HCID 19095275HCID 19095275, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-(2-Phenylpyrrol-1-yl)ethyl]acetamide (0.9 g) and 5 ml of ethylene glycol was added in succession to a solution of 1.0 g of potassium hydroxide in 10 ml of water. The reaction mixture was stirred at the boiling point for 24 hours. The cold mixture was extracted twice with 50 ml of methylene chloride each time, the organic phases were combined and extracted twice with 50 ml of 2N hydrochloric acid each time. The aqueous phases were combined, brought to a pH value of 12 by the addition of 28% sodium hydroxide solution and again extracted twice with 50 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. 0.3 g of a total of 0.6 g of crude product were dissolved in a 20-fold amount of ethanol and treated with 2 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.3 g (64%) of 1-(2-aminoethyl)-2-phenylpyrrole fumarate (1:1); m.pt.: 169°-171° C.

Workup

  1. extractionThe cold mixture was extracted twice with 50 ml of methylene chloride each time
  2. extractionextracted twice with 50 ml of 2N hydrochloric acid each time
  3. additionbrought to a pH value of 12 by the addition of 28% sodium hydroxide solution
  4. extractionagain extracted twice with 50 ml of methylene chloride each time
  5. dry with materialdried with MgSO4
  6. dissolution0.3 g of a total of 0.6 g of crude product were dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-dfb31adbf1bc4b9e8d21c8f4fff1d1a7
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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