Ethanol → 1-(2-Chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

HRID 840777Notes

Reaction equation

HRID 840777 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C:10]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O-:20])=[O:19])=[C:16](CC)[C:15]=1[NH2:25])(=O)[CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH2:32](O)[CH3:33]>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:25]1[C:15]2[CH:16]=[C:17]([C:18]([O:20][CH2:32][CH3:33])=[O:19])[CH:21]=[CH:22][C:14]=2[N:13]=[C:10]1[CH3:11]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 186810074-Acetylamino-3-amino-ethylbenzoate

Product 1

HCID 186808391-(2-Chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

Conditions

Temperature
60 °C

Procedure

2-Chlorobenzyl bromide (100 g) is added to an ethanol (750 ml) solution of 4-acetylamino-3-amino-ethylbenzoate (86.0 g) and potassium carbonate (37.3 g), and the solution is stirred for 14 hours at 60° C. Solids are separated through filtration and the filtrate is concentrated under reduced pressure. 35% hydrochloric acid (38.7 g) is added and the solution is stirred for two hours at 60° C. After solids are separated through filtration and the solution is neutralized with sodium bicarbonate, the ethanol is removed through evaporation under reduced pressure. Ethyl acetate and water are added, and extraction is performed (three times). After the organic layer is washed with water and dried, the solvent is removed through evaporation until the organic layer became. Precipitated crystals are separated through filtration and are recrystallized through ethanol. Thus, 1-(2-chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole (54.3 g ) is obtained. Furthermore, crystals are obtained by collecting and concentrating all filtrates. The crystals are recrystallized with ethanol. Thus, 1-(2-chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole (18.1 g) is obtained. 1H-NMR (CDCl3, δ): 1.39 (3H, t, J=7.1 Hz), 2.57 (3H, s), 4.37 (2H, q, J=7.1 Hz), 5.46 (2H, s), 6.41 (1H. d, J=7.8 Hz), 7.10 (1H, t, J=7.8 Hz), 7.25 (1H, t), 7.47 (1H, d, J=8.0 Hz), 7.75 (1H, d, J=8.4 Hz), 7.94 (1H, s), 8.00 (1H, d,=1.5 and 8.4 Hz).

Workup

  1. customSolids are separated through filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. addition35% hydrochloric acid (38.7 g) is added
  4. stirringthe solution is stirred for two hours at 60° C
  5. customAfter solids are separated through filtration
  6. customthe ethanol is removed through evaporation under reduced pressure
  7. additionEthyl acetate and water are added
  8. extractionextraction
  9. washAfter the organic layer is washed with water
  10. customdried
  11. customthe solvent is removed through evaporation until the organic layer
  12. customPrecipitated crystals
  13. customare separated through filtration
  14. customare recrystallized through ethanol

Sources & evidence

ORD record
ord-3bc369d39484450ba838e31ddc1b459c
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

Loading…