Hydrochloric Acid → Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate

HRID 1110806ノート

反応式

HRID 1110806 の反応式
Cl.[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:6]=2[N:5]=[CH:4]1.Cl.[CH3:16]O>>[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:16])=[O:13])=[CH:11][C:6]=2[N:5]=[CH:4]1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 148567881-methyl-1H-1,3-benzodiazole-5-carboxylic acid hydrochloride

生成物 1

HCID 965319Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate収率 43.6%

実験手順

Mass spectrum (FAB, Pos):m/z 177 (M30 +1, as a free base). ##STR11## 1-Methylbenzimidazole-5-carboxylic acid hydrochloride, 20.2 g (including inorganic matters), was added to 300 ml of methanol and 5 ml of conc. hydrochloric acid was added to the mixture followed by heating to reflux for 7 hours. The solvent was distilled off and 200 ml of water was added to the residue. At 5° to 10° C., 1 N sodium hydroxide solution was added to the mixture to adjust pH to 9 to 10 followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off under reduced pressure. The resulting crystals were washed with ether to give 4.8 g of methyl 1-methyl-benzimidazole-5-carboxylate (43.6%, based on 1,5-dimethylbenzimidazole).

後処理

  1. additionwas added to the mixture
  2. temperatureby heating
  3. temperatureto reflux for 7 hours
  4. distillationThe solvent was distilled off
  5. addition200 ml of water was added to the residue
  6. additionAt 5° to 10° C., 1 N sodium hydroxide solution was added to the mixture
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationThe solvent was distilled off under reduced pressure
  11. washThe resulting crystals were washed with ether

出典と根拠

ORDレコード
ord-a9b9faf74e854cd48ae8895d4dd77ab9
出典データセット
uspto-grants-1990_12
特許番号
US04977175

反応ノート

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