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

HRID 1696635

反応式

HRID 1696635 の反応式
[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

参加物

5

反応物 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178527798HCID 178527798、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bfc0aa21c16f4103ac46236a6e1df707
出典データセット
uspto-grants-2012_04
特許番号
US08163768B2

関連ノート

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