Nitric Acid → HCID 22938519, compound

HRID 856776Notes

Reaction equation

HRID 856776 reaction equation
[N+]([O-])(O)=O.N([O-])=O.[Na+].[CH:9]1([CH2:12][N:13]2[C:17]([CH2:18][OH:19])=[CH:16][N:15]=[C:14]2S)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:9]1([CH2:12][N:13]2[C:17]([CH2:18][OH:19])=[CH:16][N:15]=[CH:14]2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178519843HCID 178519843, compound

Product 1

HCID 22938519HCID 22938519, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.0M nitric acid (44 ml) was added sodium nitrite (135 mg), and 1-cyclopropylmethyl-5-hydroxymethyl-2-mercaptoimidazole (9.0 g) was added by portions at 0° C. The mixture was allowed to be at room temperature and the mixture was stirred for 2 hours, and water (50 ml) was added to the mixture. The mixture was neutralized with potassium carbonate at 0° C., and the solvent was distilled off under reduced pressure. Ethanol was added to the mixture, and the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added methanol-ethyl acetate, and basic silica gel was added to the mixture. This mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8), to obtain solids, which was recrystallized from diisopropyl ether-ethyl acetate, to give 1-cyclopropylmethyl-5-hydroxymethylimidazole (4.82 g) as brown crystals.

Workup

  1. additionwas added by portions at 0° C
  2. customto be at room temperature
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthanol was added to the mixture
  5. filtrationthe insolubles were filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the obtained residue was added methanol-ethyl acetate, and basic silica gel
  8. additionwas added to the mixture
  9. customThis mixture was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8)
  10. customto obtain solids, which
  11. customwas recrystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-abc9b134216541bc8f83663c89f6624f
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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