Hydrochloric Acid → 1-propyl-1H-imidazol-2-amine

HRID 1824230Notes

Reaction equation

HRID 1824230 reaction equation
C1(/C=[N:8]/[C:9]2[N:10]([CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][N:13]=2)C=CC=CC=1.Cl>>[CH2:14]([N:10]1[CH:11]=[CH:12][N:13]=[C:9]1[NH2:8])[CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22147424(E)-1-phenyl-N-(1-propylimidazol-2-yl)methanimine

Product 1

HCID 221475261-propyl-1H-imidazol-2-amineYield 56%

Procedure

A mixture of N-[(1E)-phenylmethylidene]-1-propyl-1H-imidazol-2-amine (0.92 g, 4.31 mmol) and 6N HCl (25 mL) was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated to a residue then taken up in 2M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10) to give 0.30 g (56%) of brown oil: 1H NMR (400 MHz, CDCl3) δ 6.63, 6.52, 4.00, 3.65, 1.75, 0.95; MS (ESI+) 126.7.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction was concentrated to a residue
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10)

Sources & evidence

ORD record
ord-2d668894880f419cb5fda4840c4240a2
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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