Dimethylformamide → 5-Chlorothieno[3,2-b]pyridine-3-carbaldehyde

HRID 718891

反応式

HRID 718891 の反応式
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[CH:11](NC(=O)C)[CH2:10][CH2:9][S:8]1.[C:16]([O-:19])(=O)[CH3:17].[Na+].[CH3:21][N:22]([CH3:25])C=O>>[Cl:3][C:25]1[N:22]=[C:21]2[C:17]([CH:16]=[O:19])=[CH:7][S:8][C:9]2=[CH:10][CH:11]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 14520CitioloneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

生成物 1

HCID 14762645-Chlorothieno[3,2-b]pyridine-3-carbaldehyde収率 18%

反応条件

温度
90 °C

実験手順

To the solution of phosphoryl chloride 14.9 ml (160 mmol) in dimethylformamide 45 ml, N-(2-oxotetrahydrothiophen-3-yl)acetamide 12.74 g (80 mmol) was added portion wise and stirred at 90° C. for 2 hours. The reaction mixture was poured into ice water 400 ml and followed by addition of saturated sodium acetate 500 ml. The solution was extracted by ethyl acetate 1000 ml. The organic phase was washed with water 300 ml and brine 200 ml. Then the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was crystallized by addition of ethyl acetate/ether (1:1) 200 ml and filtered. The filtrate was concentrated to obtain the title compound 3.55 g (18%).

後処理

  1. extractionThe solution was extracted by ethyl acetate 1000 ml
  2. washThe organic phase was washed with water 300 ml and brine 200 ml
  3. dry with materialThen the organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized by addition of ethyl acetate/ether (1:1) 200 ml
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-973b477edbbe406db54a4919e96ac024
出典データセット
uspto-grants-2015_11
特許番号
US09193734B2

関連ノート

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