Methyl 2-methylbenzimidazole-5-carboxylate hydrochloride → Methyl 2-methyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-6-carboxylate

HRID 1110810ノート

反応式

HRID 1110810 の反応式
Cl.[CH3:2][C:3]1[NH:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1>S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.C(O)(=O)C>[CH3:2][C:3]1[NH:4][C:5]2[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1

参加物

4

反応物 1

HCID 22154382Methyl 2-methylbenzimidazole-5-carboxylate hydrochloride

生成物 1

HCID 10797890Methyl 2-methyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-6-carboxylate収率 12%

試薬・触媒・溶媒 2

HCID 17887766Palladium barium sulphate触媒HCID 176Acetic Acid溶媒

実験手順

In an autoclave 6.8 g (30 mmols) of methyl 2-methylbenzimidazole-5-carboxylate hydrochloride, 6.0 g of 5% palladium-barium sulfate and 140 ml of acetic acid were charged and hydrogenation was carried out at 80° C. for 115 hours under 60 atms with stirring. After cooling, 5% palladium-barium sulfate was filtered off and the filtrate was distilled off under reduced pressure. After 200 ml of water was added to the residue, 1 N sodium hydroxide solution was added to the mixture at 0° to 5° C. to adjust pH to 9 to 10 followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with methylene chloride-methanol (10 : 1) to give 0.70 g (12.0%) of methyl 2-methyl-4,5,6,7-tetrahydrobenzimidazole-5-carboxylate.

後処理

  1. temperatureAfter cooling
  2. filtration5% palladium-barium sulfate was filtered off
  3. distillationthe filtrate was distilled off under reduced pressure
  4. additionAfter 200 ml of water was added to the residue, 1 N sodium hydroxide solution
  5. additionwas added to the mixture at 0° to 5° C.
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. washeluted with methylene chloride-methanol (10 : 1)

出典と根拠

ORDレコード
ord-3b666d317a6945f8b69ffc0b82f44ec5
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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