5-Nitrofurfural → HCID 178519730、化合物

HRID 1696643

反応式

HRID 1696643 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([SH:10])[NH:7][C:6]=2[C:11]=1[F:12].[H-].[Na+].[N+]([C:18]1[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1)([O-])=O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([S:10][C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)[NH:7][C:6]=2[C:11]=1[F:12]

参加物

5

反応物 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178505459HCID 178505459、化合物

生成物 1

HCID 178519730HCID 178519730、化合物収率 55.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6,7-Difluoro-1H-benzimidazole-2-thiol (0.34 g, 1.81 mmol) is suspended into 20 mL of tetrahydrofuran (THF) under argon. Then, 130 mg (2.71 mmol) of sodium hydride are added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 5-Nitro-2-furaldehyde (0.25 g, 1.81 mmol) is then added and the reaction mixture is stirred at room temperature for 3 h, upon which it is poured on ice and extracted twice 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 70 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/THF from 100/0 to 80/20 v/v; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 30 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol from 100/0 to 95/5 v/v; rate: 20 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. 0.28 g of 5-(6,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is obtained as a pale yellow meringue. LCMS-DAD-ELSD: 281(+): [M+H]+.

後処理

  1. stirringthe reaction mixture is stirred at room temperature for 3 h, upon which it
  2. additionis poured on ice
  3. extractionextracted twice 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 70 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/THF from 100/0 to 80/20 v/v; rate: 40 mL/min)
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue is purified by chromatography on a prepacked 30 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol from 100/0 to 95/5 v/v; rate: 20 mL/min)
  12. additionThe fractions containing the desired product
  13. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-e67178828c70441f999dafee5c215839
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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