Nitric Acid → (1-propyl-1H-imidazol-5-yl)methanol

HRID 1182366Notes

Reaction equation

HRID 1182366 reaction equation
[N+]([O-])(O)=O.N([O-])=O.[Na+].[OH:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][CH3:18])[C:14](S)=[N:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O>[OH:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][CH3:18])[CH:14]=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178456417(2-mercapto-1-propyl-1H-imidazol-5-yl)methanol

Product 1

HCID 22938539(1-propyl-1H-imidazol-5-yl)methanolYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.0 M nitric acid (370 ml) was added sodium nitrite (1.14 g), and then 5-hydroxymethyl-2-mercapto-1-propylimidazole (71.0 g) was portionwise added at 0° C. The mixture was returned to room temperature and stirred for 2 hours, followed by adding water (200 ml). Thereto was added potassium carbonate at 0° C. to neutralize the mixture. Then, the solvent was distilled off under reduced pressure. Ethanol was added thereto, insolubles were filtered off, and the solvent was then distilled off under reduced pressure. To the resulting residue was added methanol-ethyl acetate, and then basic silica gel was added thereto. The resulting mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8). The resulting solid was recrystallized from diisopropyl ether-ethyl acetate to give 5-hydroxymethyl-1-propylimidazole (33.6 g) as brown crystals.

Workup

  1. customwas returned to room temperature
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. additionEthanol was added
  4. filtrationinsolubles were filtered off
  5. distillationthe solvent was then distilled off under reduced pressure
  6. additionTo the resulting residue was added methanol-ethyl acetate
  7. additionbasic silica gel was added
  8. customThe resulting mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8)
  9. customThe resulting solid was recrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-858282a6f6724ab582f25fe0768b1ba0
Source dataset
uspto-grants-2007_10
Patent number
US07288654B2

Reaction notes

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