Toluene → Ethyl 1-benzyl-4-oxo-2-imidazolidinepropanoate

HRID 1589819Notes

Reaction equation

HRID 1589819 reaction equation
C([NH:8][C:9](=[O:12])[CH2:10][NH2:11])C1C=CC=CC=1.O=[CH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:28]([N:11]1[CH2:10][C:9](=[O:12])[NH:8][CH:14]1[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 82395Ethyl 4-oxobutanoateHCID 111266102-amino-N-benzylacetamide

Product 1

HCID 19770790Ethyl 1-benzyl-4-oxo-2-imidazolidinepropanoate

Procedure

A suspension of N-benzylglycinamide (35.5 g, 0.22 mol) and ethyl 4-oxobutanoate (31 g, 0.24 mol) in toluene (370 ml) was refluxed for 6 hours in a Dean-Stark apparatus. After cooling, the mixture was extracted twice with 10% sulphuric acid (200+100 ml); the aqueous extracts were neutralized with sodium hydrogen carbonate and extracted twice with toluene (250 ml each time). The organic solution was washed with water (100 ml), dried (MgSO4) and evaporated under vacuum to afford an oil which was triturated with a mixture of diethyl ether-light petroleum (1:2) to give 45 g (75%), of the title compound as a yellow solid, m.p. 60°-62° C. NMR (CDCl3): deltaH =7.5 (bs, 1H, NH); 7.30 (bs, 5H, PhH); 4.5-4.25 (ABX, 1H, CH-M); 4.13 (q, J=6.9 Hz, 2H, OCH2); 4.00 and 3.53 (ABq, J=12.4 Hz, 2H, PhCH2); 3.37 and 3.02 (ABX, J=14.9 Hz, 2H, NCH2CO); 2.65-2.30 (c.a., 2H, CH2CH2CO); 2.20-1.15 (c.a., 2H, CH2CH2CO); 1.24 (t, J=6.9 Hz, 3H, CH3). MS (E.I., 70 eV, 1.5 mA) m/z=276 (M+), 231 (M-OEt)+, 185 (M-PhCH2)+, 175 (M-C5H9O2)+, 91 (PhCH2)+.

Workup

  1. temperaturewas refluxed for 6 hours in a Dean-Stark apparatus
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted twice with 10% sulphuric acid (200+100 ml)
  4. extractionextracted twice with toluene (250 ml each time)
  5. washThe organic solution was washed with water (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum
  8. customto afford an oil which
  9. customwas triturated with a mixture of diethyl ether-light petroleum (1:2)
  10. customto give 45 g (75%)

Sources & evidence

ORD record
ord-f875fdfa55e9493f9e0f76db8eaea31b
Source dataset
uspto-grants-1993_04
Patent number
US05200406

Reaction notes

Loading…