HCID 18918877, compound → HCID 18918968, compound

HRID 1291211Notes

Reaction equation

HRID 1291211 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([C:8]2[CH:31]=[CH:30][C:11]([CH2:12][N:13]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH:23](OCC)[O:24]CC)[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([C:8]2[CH:31]=[CH:30][C:11]([CH2:12][N:13]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH:23]=[O:24])[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18918877HCID 18918877, compound

Product 1

HCID 18918968HCID 18918968, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 20% aqeuous acetic acid (10 ml) was dissolved ethyl 1-[4-(4-chlorobenzoyl)benzyl]-4-(diethoxymethyl)-imidazole-5-carboxylate (1.20 g) and the mixture was stirred at room temperature for 8 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed serially with water, saturated aqueous NaHCO3 solution, and water, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1) to provide the title compound as white powder (671 mg; yield 67%). 1H-NMR (CDCl3) δ: 1.38(3H,t,J=7.OHz), 4.41(2H,q,J=7.OHz), 5.66(2H,s), 7.26(2H,d,J=8.8Hz), 7.46(2H,d,J=8.8Hz), 7.70-7.79(5H,m), 10.42(1H,s).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed serially with water, saturated aqueous NaHCO3 solution, and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4d9aa4fcca02490aaa85d3302730cae7
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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