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

HRID 344754ノート

反応式

HRID 344754 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-bfe19a96832d4d6992639cb98800a750
出典データセット
uspto-grants-1991_10
特許番号
US05053422

反応ノート

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