HCID 18919005, compound → HCID 18919292, compound

HRID 1291210Notes

Reaction equation

HRID 1291210 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]([CH:18](OCC)[O:19]CC)=[C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[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:3]=[CH:4][C:5]([C:6]([C:8]2[CH:31]=[CH:30][C:11]([CH2:12][N:13]3[C:17]([CH:18]=[O:19])=[C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 18919005HCID 18919005, compound

Product 1

HCID 18919292HCID 18919292, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 20% aqueous acetic acid (15 ml) was dissolved ethyl 1-[4-(4-chlorobenzoyl)benzyl]-5-(diethoxymethyl)-imidazole-4-carboxylate (1.70 g) and the solution was stirred at room temperature for 23 hours. This solution 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 distilled off under reduced pressure to provide the title compound as white powder (1.37g; yield 95%). 1H-NMR (CDCl3) δ: 1.45(3H,t,J=7.2Hz), 4.47(2H,q,J=7.2Hz), 5.65(2H,s), 7.28(2H,d,J=8.4Hz), 7.46(2H,d,J=8.4Hz), 7.69-7.77(5H,m), 10.51(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 distilled off under reduced pressure

Sources & evidence

ORD record
ord-3742fefe3c434695b696b543cd9f38cf
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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