Ethyl 2,3-dihydro-5-methyl-epsilon-2-dioxo-1H-imidazole-4-hexanoate → HCID 13590259, compound

HRID 2231383Notes

Reaction equation

HRID 2231383 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:18])[NH:5][C:6]=1[C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:19]([O:23][C:24]([O-:26])=O)(=O)OC>>[CH3:15][O:14][C:12]([N:5]1[C:6]([C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:2]([CH3:1])[N:3]([C:24]([O:23][CH3:19])=[O:26])[C:4]1=[O:18])=[O:13]

Participants

3

Reactant 2

HCID 2166009Ethyl 2,3-dihydro-5-methyl-epsilon-2-dioxo-1H-imidazole-4-hexanoateHCID 86742518HCID 86742518, compound

Product 1

HCID 13590259HCID 13590259, compoundYield 76.6%

Conditions

Temperature
90 °C

Procedure

A mixture of 1.88 g (7.4 mmol) of 4-methyl-5-(5-ethoxycarbonylpentanoyl)-4-imidazolin-2-one and 20 ml methyl pyrocarbonate was heated to 90° C., and stirred for 1.5 hours whereupon a complete solution was obtained. After removal of the volatiles in vacuo, the oily residue was treated with 20 ml hexanes to give a white solid which was collected by filtration and washed with two 5 ml portions of hexanes. Recrystallization from 100 ml ethyl ether gave 2.1 g (76.6%) of the title compound; m.p. 74°-76° C.; 1H-NMR (CDCl3): 1.27 (t, 3, OCH2CH3), 1.58-1.76 (m, 4, 2CH2 's), 2.33 (t, 2, CH2), 2.38 (s, 3, CH3), 2.57 (t, 2, CH2), 3.98 (s, 3, NCOOCH3), 4.01 (s, 3, NCOOCH3) and 4.14 ppm (q, 2, OCH2CH3); 13C-NMR δ (CDCl3) 11.9, 14.2, 23.1, 24.3, 34.0, 41.8, 54.8, 55.1, 60.3, 120.9, 126.5, 146.4, 149.9, 150.2, 173.2, and 192.6 ppm.

Workup

  1. customwas obtained
  2. customAfter removal of the volatiles in vacuo
  3. additionthe oily residue was treated with 20 ml hexanes
  4. customto give a white solid which
  5. filtrationwas collected by filtration
  6. washwashed with two 5 ml portions of hexanes
  7. customRecrystallization from 100 ml ethyl ether

Sources & evidence

ORD record
ord-655b0935f54a4ed1a4ffa7a85c5ffef5
Source dataset
uspto-grants-1988_11
Patent number
US04782165

Reaction notes

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