Pyridine → ethyl (E)-3-[2-n-butyl-1-{(5-carbomethoxy-2-thienyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2propenoate

HRID 2399243Notes

Reaction equation

HRID 2399243 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[S:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:17]=2)[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C([CH:25]([CH2:31][C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])(O)=O.N1CCCCC1.N1C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[S:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:17]=2)[C:7](/[CH:10]=[C:25](\[CH2:31][C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8082PiperidineHCID 14952883Ethyl 2-carboxy-3-(2-thienyl)propionateHCID 193873192-n-Butyl-1-[(5-carbomethoxy-2-thienyl)methyl]imidazol-5-carboxaldehyde

Product 1

HCID 86748961ethyl (E)-3-[2-n-butyl-1-{(5-carbomethoxy-2-thienyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2propenoateYield 60.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-n-butyl-1-[(5-carbomethoxy-2-thienyl)methyl]imidazol-5-carboxaldehyde (0.5 g, 1.66 mmol), ethyl 2-carboxy-3-(2-thienyl)propionate (1.14 g, 4.99 mmol), piperidine (0.155 g, 1.83 mmol), 0.5 ml of pyridine in 50 ml of benzene were refluxed for 18 hours under argon in the presence of a Dean-Stark trap. The crude product was flash chromatographed over silica gel eluting with ethyl acetate/hexane (1:1) to give 0.474 g (49%) of ethyl (E)-3-[2-n-butyl-1-{(5-carbomethoxy-2-thienyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2propenoate.

Workup

  1. temperaturewere refluxed for 18 hours under argon in the presence of a Dean-Stark trap
  2. customchromatographed over silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-73319a8adb4946a584a97a4782f63656
Source dataset
uspto-grants-1995_09
Patent number
US05447949

Reaction notes

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