Potassium Carbonate → HCID 22938533, compound

HRID 856794Notes

Reaction equation

HRID 856794 reaction equation
N([O-])=O.[Na+].[OH:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]#[CH:14])[C:10](S)=[N:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>O>[OH:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]#[CH:14])[CH:10]=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178456415HCID 178456415, compound

Product 1

HCID 22938533HCID 22938533, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.0M nitric: acid (134 ml) was added sodium nitrite (411 mg), and 5-hydroxymethyl-2-mercapto-1-(2-propyn-1-yl)imidazole (25.0 g) was added by portions to the mixture. After the mixture was allowed to be at room temperature and stirred for 1 hour, water (60 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, 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), and the obtained solid was recrystalized from hexane-ethyl acetate, to give 5-hydroxymethyl-1-(2-propyn-1-yl)imidazole (8.46 g) as yellow crystals.

Workup

  1. additionwas added by portions to the mixture
  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. customthe obtained solid was recrystalized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-98147a8fe11c4f91ace9f05d8e250ad6
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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