Ethanol → Ethyl 4,5,6,7-tetrahydro-1H-benzo[d]imidazole-6-carboxylate

HRID 1585214

반응식

HRID 1585214 반응식
S([O-])([O-])(=O)=O.[CH2:6]([O:8][C:9]([C:11]1[CH:19]=[CH:18][C:14]2[N:15]=[CH:16][NH:17][C:13]=2[CH:12]=1)=[O:10])[CH3:7].C(O)C>[C].[Pd].[H][H]>[CH2:6]([O:8][C:9]([CH:11]1[CH2:19][CH2:18][C:14]2[N:15]=[CH:16][NH:17][C:13]=2[CH2:12]1)=[O:10])[CH3:7]

참가 물질

6

반응물 3

HCID 702EthanolHCID 1117Sulfate IonHCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

생성물 1

HCID 21222281Ethyl 4,5,6,7-tetrahydro-1H-benzo[d]imidazole-6-carboxylate

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 178418361HCID 178418361, 화합물용매

실험 절차

A mixture of 10.0 g of sulfate of benzimidazole-5-carboxylic ethyl ester, 5.0 g of 5% palladium-carbon catalyst, and 100 ml of ethanol was stirred in hydrogen for five hours under the conditions of 135° C. and 50 kg/cm2, cooled, then filtered to separate the catalyst, and distilled to expel the ethanol. The residue of the distillation was neutralized with an aqueous sodium bicarbonate solution and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and then distilled to expel chloroform and obtain 6.9 g of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic ethyl ester. This ester and 200 ml of 6N hydrochloric acid added thereto were refluxed together for seven hours. The hydrochloric acid solution was concentrated to dryness, crystallized by addition of acetone, separated by filtration, and then dried to obtain 6.9 g of hydrochloride of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. customto separate the catalyst
  4. distillationdistilled
  5. distillationThe residue of the distillation
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  8. distillationdistilled

출처 및 근거

ORD 기록
ord-44eadcf7d79240e28e635913ec9e072a
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05936098

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