Sodium Methoxide → 2-Methoxycyclohepta[d]imidazole

HRID 1194290Notes

Reaction equation

HRID 1194290 reaction equation
CS[C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[C:6]2[N:7]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[C:6]2[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 151230382-Methylthiocycloheptimidazole

Product 1

HCID 200643812-Methoxycyclohepta[d]imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First, 3 g of 2-methylthiocycloheptimidazole as synthesized according to Synthetic example 1 (c) with reference to the method disclosed in Bulletin of the Chemical Society of Japan, volume 33, No. 1, pages 56 to 58 (1960) was added to 50 ml of methanol, and 1 g of sodium methoxide was further added thereto. After reflux with heating for 10 hours, the solvent was distilled away, and 50 ml of benzene was added to the residue. The insoluble matters were filtered out, and the filtrate was concentrated. The resulting crystals were purified by silica gel column chromatography using ethyl acetate as a developing solvent.

Workup

  1. additionwas further added
  2. temperatureAfter reflux
  3. temperaturewith heating for 10 hours
  4. distillationthe solvent was distilled away
  5. addition50 ml of benzene was added to the residue
  6. filtrationThe insoluble matters were filtered out
  7. concentrationthe filtrate was concentrated
  8. customThe resulting crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f77651c85adf4118b530a910d70c8086
Source dataset
uspto-grants-1989_03
Patent number
US04814265

Reaction notes

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