Methanol → Methyl 1-hexylimidazole-5-carboxylate

HRID 1655084ノート

反応式

HRID 1655084 の反応式
[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[CH2:14](I)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH3:21]O>>[CH2:14]([N:1]1[C:5]([C:6]([O:8][CH3:21])=[O:7])=[CH:4][N:3]=[CH:2]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

参加物

5

反応物 4

HCID 887Methanol3 回HCID 1118Sulfuric AcidHCID 125271-IodohexaneHCID 14080Imidazole-4-carboxylic acid

生成物 1

HCID 20077582Methyl 1-hexylimidazole-5-carboxylate収率 7.5%

実験手順

Imidazole-5-carboxylic acid (10.0 g, 89 mmol) was dissolved in methanol (185 ml) and concentrated sulphuric acid (10 ml) was added dropwise. The mixture was heated under reflux for two days. After cooling in ice and neutralising with dilute sodium hydroxide solution the solvents were removed by evaporation. The white solid produced was suspended in methanol (70 ml) and hexyl iodide (26.3 ml, 178 mmol) in methanol (30 ml) was added. After heating under reflux overnight, the mixture was cooled and filtered through a pad of diatomaceous earth, washing well with methanol. The filtrate was concentrated and the residue purified by column chromatography, eluting with 1.5% methanol/dichloromethane (v/v), to give methyl 1-hexylimidazole-5-carboxylate (1.4 g; 7.5% yield), as an oil;

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two days
  3. temperatureAfter cooling in ice
  4. customneutralising with dilute sodium hydroxide solution the solvents were removed by evaporation
  5. customThe white solid produced
  6. temperatureAfter heating
  7. temperatureunder reflux overnight
  8. temperaturethe mixture was cooled
  9. filtrationfiltered through a pad of diatomaceous earth
  10. washwashing well with methanol
  11. concentrationThe filtrate was concentrated
  12. customthe residue purified by column chromatography
  13. washeluting with 1.5% methanol/dichloromethane (v/v)

出典と根拠

ORDレコード
ord-02980b4c483840b08d49ba23e693bf23
出典データセット
uspto-grants-1995_04
特許番号
US05410064

反応ノート

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