HCID 54544079, compound → 1-(prop-2-en-1-yl)-1H-imidazol-2-amine

HRID 741711Notes

Reaction equation

HRID 741711 reaction equation
CN(C=[N:5][C:6]1[N:7]([CH2:11][CH:12]=[CH2:13])[CH:8]=[CH:9][N:10]=1)C>Cl>[NH2:5][C:6]1[N:7]([CH2:11][CH:12]=[CH2:13])[CH:8]=[CH:9][N:10]=1

Participants

3

Procedure

2-(Dimethylaminomethylene)amino-1-(2-propenyl)imidazole (0.2 g) was dissolved in 6N hydrochloric acid (5 ml), and the solution was heated under reflux for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in aqueous saturated sodium carbonate solution (1 ml). The solution was concentrated under reduced pressure, the organic compounds were extracted with chloroform, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=20: 1:0.1) to give 2-amino-1-(2-propenyl)imidazole. This compound was dissolved in dichloromethane, and 4N hydrochloric acid-ethyl acetate (2 ml) was added to form its hydrochloric acid salt. The salt was recrystallized from acetonitrile to give 2-amino-1-(2-propenyl)imidazole hydrochloride (0.19 g, Yield: 71%) as pale yellow needles.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in aqueous saturated sodium carbonate solution (1 ml)
  5. concentrationThe solution was concentrated under reduced pressure
  6. extractionthe organic compounds were extracted with chloroform
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=20: 1:0.1)

Sources & evidence

ORD record
ord-1e6a88c6fc1e4f0ea5668eff0b407ac1
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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