Ethyl 8-bromooctanoate → HCID 22916350, compound

HRID 1376353Notes

Reaction equation

HRID 1376353 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:33]([O:32][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][N:12]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[CH:11]1)=[O:31])[CH3:34]

Participants

3

Reactant 2

HCID 264813Ethyl 8-bromooctanoateHCID 14100143HCID 14100143, compound

Product 1

HCID 22916350HCID 22916350, compoundYield 83.6%

Procedure

4,5-Bis(4-methoxyphenyl)imidazole (1.8 g) (J. Med. Chem., 1974, 17, 1182-8) and ethyl 8-bromooctanoate (3.2 g) were reacted in a method similar to Example 9. Colnmn chromatography on silica gel eluted with a dichloro-methane:ethanol gradient gave 1-(7-ethoxycarbonyl-heptyl)- 4,5-bis(4-methoxyphenyl)imidazole (2.42 g, 83%) as an oil. Found: C, 72.30; H, 7.72; N, 6.21%; C27H34N20 4 requires: C, 71.97; H, 7.61; N, 6.22%.

Workup

  1. washColnmn chromatography on silica gel eluted with a dichloro-methane

Sources & evidence

ORD record
ord-84aa31ebf7754107905d03f9ce78c9b7
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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