Ethylene Glycol → HCID 15617195, compound

HRID 2351627Notes

Reaction equation

HRID 2351627 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)C.C(O)CO.[OH-].[K+]>O>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[N:6]([CH2:5][C:4]([OH:3])=[O:24])[C:7]3=[N:8][CH:9]=[CH:10][CH:11]=[C:12]3[N:13]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 14390491HCID 14390491, compound

Product 1

HCID 15617195HCID 15617195, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[3-[(4-methoxybenzoyl)amino]-2-pyridinyl] glycine ethyl ester (32 g, 0.1 mole) and 167 ml of ethylene glycol was heated at reflux for 11/2 hr. After cooling, potassium hydroxide (8.4 g) in 40 ml of water was added, and the reaction mixture was heated at reflux for 1 hr. The solution was filtered to remove yellow precipitate, the filtrate was diluted with 650 ml of water, and acidified with 3N hydrochloric acid. The solid which formed, was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight to give 25.5 g (90.1%) yield). A 0.5-g sample was recrystallized from ethanol, collected by filtration, washed with cold ethanol and water, and dried under high vacuum at 70° C. over 2 days to give 0.47 g of crystals, mp 260°-63° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hr
  3. temperatureAfter cooling
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 1 hr
  6. filtrationThe solution was filtered
  7. customto remove yellow precipitate
  8. additionthe filtrate was diluted with 650 ml of water
  9. customThe solid which formed
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried under high vacuum at 50° C. overnight
  13. customto give 25.5 g (90.1%)
  14. customyield)
  15. customA 0.5-g sample was recrystallized from ethanol
  16. filtrationcollected by filtration
  17. washwashed with cold ethanol and water
  18. customdried under high vacuum at 70° C. over 2 days

Sources & evidence

ORD record
ord-4898f3cdf802497cbc53e0f22bfcc2b2
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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