2-Chloro-3-pyridinecarboxaldehyde → 2-((4-Chlorophenyl)sulfonyl)nicotinaldehyde

HRID 41869

反応式

HRID 41869 の反応式
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 23664783Sodium 4-chlorobenzenesulfinate

生成物 1

HCID 593805922-((4-Chlorophenyl)sulfonyl)nicotinaldehyde収率 46.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-3-pyridinecarboxaldehyde (5.0 g, 35.0 mmol) and 4-chlorobenzenesulfinic acid sodium salt (7.75 g, 38.8 mmol) were dissolved in DMSO (120 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 8.1 g of crude material. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.62 g (61%) of the desired product as a white powdery solid (MP=100.5-101° C.; IR=1698 cm−1; HPLC=8.00 min>99%).

後処理

  1. temperatureUpon cooling to ambient the mixture
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customto afford 8.1 g of crude material
  7. customThe crude compound was pre-absorbed onto silica
  8. custompurified
  9. customby dry pad suction column chromatography
  10. washeluting with heptane using an EtOAc gradient

出典と根拠

ORDレコード
ord-eaf7250bb33344d6979b76e7a6d84fa3
出典データセット
uspto-grants-2013_09
特許番号
US08536158B2

関連ノート

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