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

HRID 654125Notes

Reaction equation

HRID 654125 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 (31g, 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-227b59fa59894dfeb76572af9f9223ee
Source dataset
uspto-grants-1992_07
Patent number
US05130319

Reaction notes

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