ethyl 1H-imidazole-2-carboxylate → HCID 178470170, compound

HRID 1107040Notes

Reaction equation

HRID 1107040 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH:14](C1NC=C(C(OCC)=O)N=1)[C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C1C=CC=C2C=1CC(Br)C2=O)=O)C1C=CC=CC=1.[CH2:52]([O:54][C:55]([C:57]1[NH:58][CH:59]=[CH:60][N:61]=1)=[O:56])[CH3:53]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:9]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH:14]([C:59]1[N:58]=[C:57]([C:55]([O:54][CH2:52][CH3:53])=[O:56])[NH:61][CH:60]=1)[C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 549404ethyl 1H-imidazole-2-carboxylateHCID 187906544-Benzylcarbamoyl-2-bromo-1-indanoneHCID 178469882HCID 178469882, compound

Product 1

HCID 178470170HCID 178470170, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Benzylcarbamoyl-2-(ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: a mixture of 0.5 g of 4-benzylcarbamoyl-2-bromo-1-indanone, 0.37 g of 2-ethoxycarbonylimidazole and 10 ml of toluene is heated at reflux for 12 hours. The reaction mixture is concentrated on a rotary evaporator. Dichloromethane is added to the evaporation residue, filtration is carried out and the filtrate is washed with distilled water, dried over sodium sulphate and evaporated on a rotary evaporator. The brown oil obtained (0.26 g) is purified by chromatography on a silica column (diameter: 1.5 cm, height: 30 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. The foamy product obtained is triturated with 5 ml of ethyl acetate, filtered and the solid is washed-with ethyl acetate (2 x 5 ml) and dried at 50° C. under vacuum (1 mm Hg; 0.13 kPa). 0.07 g of 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of an orange solid melting at 218° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 12 hours
  3. concentrationThe reaction mixture is concentrated on a rotary evaporator
  4. additionDichloromethane is added to the evaporation residue, filtration
  5. washthe filtrate is washed with distilled water
  6. dry with materialdried over sodium sulphate
  7. customevaporated on a rotary evaporator
  8. customThe brown oil obtained (0.26 g)
  9. customis purified by chromatography on a silica column (diameter: 1.5 cm, height: 30 cm), elution
  10. customThe foamy product obtained
  11. customis triturated with 5 ml of ethyl acetate
  12. filtrationfiltered
  13. customdried at 50° C. under vacuum (1 mm Hg; 0.13 kPa)

Sources & evidence

ORD record
ord-e2105b26fd564e1e8ebf4102b049e0b6
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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