Ethyl 8-bromooctanoate → HCID 22916405, compound

HRID 265381Notes

Reaction equation

HRID 265381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][NH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:11]=[CH:10][N:9]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 264813Ethyl 8-bromooctanoateHCID 124673084,5-Bis(2-chlorophenyl)imidazole

Product 1

HCID 22916405HCID 22916405, compoundYield 23.7%

Procedure

4,5-Bis(2-chlorophenyl)imidazole (1.2 g) (Chem. Ber., 1959, 92, 338-343) and ethyl 8-bromooctanoate (2.1 g) were reacted in a method similar to Example 9. Column chromatography on silica gel eluted with a dichloro-methane:ethanol gradient gave 4,5-bis(2-chlorophenyl)-1-(7-ethoxycarbonyl-heptyl)imidazole (0.45 g, 23.7%) as an oil. NMR d (CDCl3) 1.0-1.8(11H, m, 4×CH2, CH3), 2.2(2H, t, CH2C=O), 3.8 (2H, m, N--CH2), 4.1(2H, q, CH2OC=O), 7.1-7.45 (8H, m, ArH), 7.69 (1H, s, N=CH) ppm

Workup

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

Sources & evidence

ORD record
ord-a4fc1611274949f3bcf221581d54a425
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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