Triethylamine → HCID 23299969, compound

HRID 1952749Notes

Reaction equation

HRID 1952749 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[NH:10])OC)[CH:2]=1.Cl.C([O:14][C:15](=O)[C@H:16]([CH3:18])[NH2:17])C.C(N(CC)CC)C>O1CCCC1>[CH3:18][CH:16]1[C:15](=[O:14])[NH:10][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 103293433-Pyridinecarboximidic acid, methyl ester

Product 1

HCID 23299969HCID 23299969, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of methyl pyridine-3-carboximidate (10.6 g), alanine ethyl ester monohydrochloride (10 g), triethylamine (8.4 ml) and tetrahydrofuran (250 ml) was heated under reflux under nitrogen for 5 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and the solvent removed in vacuo. The residue was triturated with a 1:1 mixture of ether and ethyl acetate, and the resulting solid was collected by filtration and washed with ether. The two crops of solid were combined, suspended in water (130 ml), and the mixture was stirred at ambient temperature for 1 hour. The resulting solid was collected by filtration and dried in vacuo to give 4-methyl-2-(3-pyridyl)-2-imidazolin-5-one as a yellow solid (4.9 g), m.p. 238-241° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 5 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with tetrahydrofuran
  5. customthe solvent removed in vacuo
  6. customThe residue was triturated with a 1:1 mixture of ether and ethyl acetate
  7. filtrationthe resulting solid was collected by filtration
  8. washwashed with ether
  9. filtrationThe resulting solid was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-212e5cacbcbf4ad9a1b097fedc724cab
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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