2,5-Hexanedione → 7-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698550노트

반응식

HRID 1698550 반응식
[NH2:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:18][C:17]1[N:1]([C:2]2[C:7]3[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 80352,5-HexanedioneHCID 516892Sodium BicarbonateHCID 596354197-Amino-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

생성물 1

HCID 672731377-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one수율 68.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
90 °C

실험 절차

To a suspension of 257 mg (1.57 mmol) of 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one in 2 mL of acetic acid was added 0.18 mL (1.57 mmol) of 2,5-hexanedione, the mixture was stirred at 90° C. for 1 hour. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-50% ethylacetate/n-hexane gradient mixture to give 258 mg (68%) of the title compound.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 25-50% ethylacetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-d60e54c0ab7f42a5b2bacd754876cdb7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

반응 노트

불러오는 중…