Ethyl 8-bromooctanoate → 2-Benzyl-1-(7-ethoxycarbonylheptyl)-4,5-diphenylimidazole

HRID 1376348Notes

Reaction equation

HRID 1376348 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[CH2:1]([C:8]1[N:12]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 264813Ethyl 8-bromooctanoateHCID 124032122-Benzyl-4,5-diphenylimidazole

Product 1

HCID 229163402-Benzyl-1-(7-ethoxycarbonylheptyl)-4,5-diphenylimidazoleYield 52.6%

Procedure

2-Benzyl-4,5-diphenylimidazole (3.3 g) (Weiss, M, J. ,Am. Chem. Soc., 1952, 74, 5193-5) was reacted with ethyl 8-bromooctanoate as in Example 9. Colnmn chromatography on silica gel eluted with a dichloromethane:ethanol gradient followed by distillation at 200° C./0.1 torr to remove volatile impurities gave a yellow oil. Recrystallisation from hexane gave 2-benzyl-1-(7-ethoxycarbonylheptyl)-4,5-diphenylimidazole (2.69 g, 52.6%) as a white solid, m.p. 82°-3°. Found: C, 80.35; H, 7.58; N, 6.08%; C32H36N2O2 requires: C, 79.96; H, 7.55; N. 5.83%.

Workup

  1. washColnmn chromatography on silica gel eluted with a dichloromethane
  2. distillationethanol gradient followed by distillation at 200° C./0.1 torr
  3. customto remove volatile impurities
  4. customgave a yellow oil
  5. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-39a55b96ca6042c0b8fecc552a1c6102
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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