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

HRID 344754Notes

Reaction equation

HRID 344754 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 of 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 of 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-bfe19a96832d4d6992639cb98800a750
Source dataset
uspto-grants-1991_10
Patent number
US05053422

Reaction notes

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