Ethyl levulinate → 1H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-

HRID 1589803Notes

Reaction equation

HRID 1589803 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].O=[C:10]([CH3:18])[CH2:11][CH2:12][C:13](OCC)=[O:14]>O>[O:5]=[C:4]1[CH2:3][N:2]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2([CH3:18])[NH:6]1

Participants

5

Reactant 3

HCID 10883Ethyl levulinateHCID 14798Sodium HydroxideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 30795901H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-Yield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of glycinamide hydrochloride (18.4 g, 0.166 mol) in water (200 ml), adjusted to pH 9.5 with 10% sodium hydroxide (about 60 ml), ethyl 4-oxopentanoate (20 g, 0.139 mol) was added. The solution was refluxed for 24 hours. After cooling the solvent was evaporated under vacuum and the residue was chromatographed over silica gel (dichloromethane-methanol 9:1) to afford 4.5 g (21%) of the title compound, m.p. 187°-189° C. NMR (CDCl3): deltaH =4.17 and 3.53 (ABq, J=16 Hz, 2H, NCH2CO), 1.5 (s, 3H, CH3). MS (E.I., 70 eV, 1.5 mA) m/z=154 (M+), 139 (M-CH3)+, 111 (M-CONH)+.

Workup

  1. additionwas added
  2. temperatureThe solution was refluxed for 24 hours
  3. temperatureAfter cooling the solvent
  4. customwas evaporated under vacuum
  5. customthe residue was chromatographed over silica gel (dichloromethane-methanol 9:1)

Sources & evidence

ORD record
ord-b92da8d0d2214a0c9b4800118f645ee9
Source dataset
uspto-grants-1993_04
Patent number
US05200406

Reaction notes

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