Diethyl Oxalate → HCID 57565040, compound

HRID 1726903Notes

Reaction equation

HRID 1726903 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[CH2:11]([O:18][CH2:19][C:20]([O:22]CC)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br.[C:28]1([N:34]2[CH2:38][CH2:37][N:36]=[C:35]2[NH2:39])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:36]2[CH2:37][CH2:38][N:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:35]2=[N:39][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 2817952HCID 2817952, compound

Product 1

HCID 57565040HCID 57565040, compoundYield 11%

Procedure

Reaction of the adduct of diethyl oxalate (7.06 g, 48.3 mmol), ethyl benzyloxyacetate (9.38 g, 48.3 mmol) and sodium hydride (2.12 g of a 60% dispersion in mineral oil, 53.1 mmol) with 1-phenyl-4,5-dihydro-1H-imidazol-2-amine hydrobromide (11.70 g, 48.3 mmol) as described for intermediate 1 gave 1.99 g (11% yield) of the title ester as white crystals; mp 132-134° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (3H, t, J=7.1 Hz, CH3), 4.23-4.29 (4H, m, 2×CH2), 4.35 (2H, q, J=7.1 Hz, OCH2), 5.18 (2H, s, OCH2), 7.16 (1H, m, aromatic), 7.3-7.53 (7H, m, aromatics), 7.73 (2H, m, aromatics). Anal. Calcd for C22H21N3O4: C, 67.50; H, 5.40; N, 10.73. Found: C, 67.44; H, 5.68; N, 10.73.

Sources & evidence

ORD record
ord-ad8dbddbd0f246eb828bf52e586f8fd3
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

Loading…