Hydrochloric Acid → HCID 70511522, compound

HRID 223508Notes

Reaction equation

HRID 223508 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][C:14]#N)=[C:11]([Cl:16])[N:10]=[C:9]1[CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH2:22].[CH2:23]([OH:25])[CH3:24]>>[ClH:16].[CH2:1]([N:8]1[C:12]([CH2:13][C:14]([O:25][CH2:23][CH3:24])=[O:22])=[C:11]([Cl:16])[N:10]=[C:9]1[CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 13022621HCID 13022621, compound

Product 1

HCID 70511522HCID 70511522, compound

Procedure

1 g of 1-benzyl-2-n-butyl-4-chloro-5-cyanomethylimidazole was heated in 20 ml of ethanol containing 1 g of hydrogen chloride in a sealed tube at 100° C. for 2 hours. 0.5 ml of water was added to the reaction solution, which was then boiled for 1 hour and evaporated to dryness under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate and, after washing with aqueous sodium bicarbonate, the ethyl acetate layer was evaporated to dryness, and chromatographed on a column of 30 g of silica gel. The column was eluted with benzene-ethyl acetate (4:1), and the main fractions were evaporated to dryness. The residue was dissolved in 1 ml ethanol saturated with hydrogen chloride, and crystallized by adding petroleum ether. After further adding ethyl acetate to separate out in the fully crystallized condition, there was obtained 300 mg of ethyl 1-benzyl-2-n-butyl-4-chloroimidazole-5-acetate hydrochloride. m.p. 101°-103° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  3. washafter washing with aqueous sodium bicarbonate
  4. customthe ethyl acetate layer was evaporated to dryness
  5. customchromatographed on a column of 30 g of silica gel
  6. washThe column was eluted with benzene-ethyl acetate (4:1)
  7. customthe main fractions were evaporated to dryness
  8. dissolutionThe residue was dissolved in 1 ml ethanol saturated with hydrogen chloride
  9. customcrystallized
  10. additionby adding petroleum ether
  11. additionAfter further adding ethyl acetate
  12. customto separate out in the fully crystallized condition

Sources & evidence

ORD record
ord-08bba501b07c49b18c8f17c2cf1a14d4
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

Loading…