Triethylamine → HCID 23300038, compound

HRID 1952751Notes

Reaction equation

HRID 1952751 reaction equation
Cl.[C:2](=[NH:11])(OC)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C([O:15][C:16](=O)[C@H:17]([CH3:19])[NH2:18])C.C(N(CC)CC)C>O1CCCC1>[CH3:19][CH:17]1[C:16](=[O:15])[NH:11][C:2]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 5743287Methyl benzimidate hydrochloride

Product 1

HCID 23300038HCID 23300038, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl benzimidate monohydrochloride (5 g), alanine ethyl ester monohydrochloride (4.77 g), triethylamine (8.5 ml) and tetrahydrofuran (130 ml) was stirred and heated under reflux under nitrogen for 5.5 hours, then the solvent was removed in vacuo. The residue was triturated with a 1:1 mixture of ether and ethyl acetate, and the resulting yellow solid was collected by filtration and suspended in water (100 ml). The mixture was stirred at ambient temperature for 1 hour, then the resulting solid was collected by filtration, and dried in vacuo to give 4-methyl-2-phenyl-2-imidazolin-5-one as a yellow solid (2.58 g), m.p. 165° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux under nitrogen for 5.5 hours
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with a 1:1 mixture of ether and ethyl acetate
  5. filtrationthe resulting yellow solid was collected by filtration
  6. stirringThe mixture was stirred at ambient temperature for 1 hour
  7. filtrationthe resulting solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-09f82a388a514aaca1f767bacdf9f5e7
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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