5-Nitrofurfural → 5-[(5,6-Dichloro-1H-benzimidazol-2-yl)sulfanyl]furan-2-carbaldehyde

HRID 1696635

반응식

HRID 1696635 반응식
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[NH:6][C:7]([SH:9])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[N+]([C:18]1[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1)([O-])=O>O1CCCC1>[Cl:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([S:9][C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[N:6][C:5]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178527798HCID 178527798, 화합물

생성물 1

HCID 714239795-[(5,6-Dichloro-1H-benzimidazol-2-yl)sulfanyl]furan-2-carbaldehyde수율 65.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5,6-Dichloro-1H-benzimidazole-2-thiol (1.0 g, 4.56 mmol) is suspended into 50 mL of tetrahydrofuran under argon. Then, 0.33 g (6.85 mmol) of sodium hydride is added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 5-Nitro-2-furaldehyde (0.64 g, 4.57 mmol) is then added and the reaction mixture is stirred at room temperature for 1 h, upon which it is poured on ice and extracted 3 times with ethyl acetate. The organic extracts are combined, washed with brine, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a prepacked 200 g 15-40 μm silica gel cartridge (eluting solvent: ethyl acetate/cyclohexane 50/50 v/v; rate: 50 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is triturated in diisopropyl ether, filtered and dried under reduced pressure. 0.93 g of 5-(5,6-dichloro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is obtained as a yellow powder. mp: 170° C.

후처리

  1. stirringthe reaction mixture is stirred at room temperature for 1 h, upon which it
  2. additionis poured on ice
  3. extractionextracted 3 times with ethyl acetate
  4. washwashed with brine
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography on a prepacked 200 g 15-40 μm silica gel cartridge (eluting solvent: ethyl acetate/cyclohexane 50/50 v/v; rate: 50 mL/min)
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue is triturated in diisopropyl ether
  12. filtrationfiltered
  13. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-bfc0aa21c16f4103ac46236a6e1df707
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163768B2

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