Hydrochloric Acid → 1-(2-Aminoethyl)-4,5-diphenylimidazole

HRID 362896Notes

Reaction equation

HRID 362896 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:13]=[CH:12]2)C(=O)C2=CC=CC=C12.Cl>CO>[NH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 539687861-(2-Phthalimidoethyl)-4,5-diphenylimidazole

Product 1

HCID 540605101-(2-Aminoethyl)-4,5-diphenylimidazoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 3): 80% Hydrazine monohydrate (0.062 ml, 1.3 mmol) was added to a solution of 1-(2-phthalimidoethyl)-4,5-diphenylimidazole (0.32 g, 0.8 mmol) in methanol (20 ml) under refluxing. The reaction mixture was refluxed for 1 hour, then cooled. The mixture was made acidic slightly with 6N HCl and then filtered to remove phthalhydrazide. The filtrate was concentrated and then the residue was suspended in 2N NaOH. The suspended mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and concentrated. The precipitates were recrystallized (ethyl acetate/hexane) to give 1-(2-aminoethyl)-4,5-diphenylimidazole (88.1%): mp 96°-98° C.

Workup

  1. temperatureunder refluxing
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove phthalhydrazide
  6. concentrationThe filtrate was concentrated
  7. extractionThe suspended mixture was extracted with chloroform
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe precipitates were recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c315d63eb0ae4df4929d670e9e9e8ac0
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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