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

HRID 718891Notes

Reaction equation

HRID 718891 reaction equation
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

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14520CitioloneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

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

Conditions

Temperature
90 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-973b477edbbe406db54a4919e96ac024
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

Loading…