Pyridine → 1083317-25-2

HRID 2407714Notes

Reaction equation

HRID 2407714 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[S:9])[NH2:8].N1C=CC=CC=1.Br[CH:17]([CH:20]=O)[CH:18]=[O:19]>O1CCCC1.CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:9][C:17]([CH:18]=[O:19])=[CH:20][N:8]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 749452-BromopropanedialHCID 1549499Pyridine-2-carbothioamide

Product 1

HCID 534037721083317-25-2Yield 38.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridine-2-carbothioamide (4.5 g) was dissolved in tetrahydrofuran (40 mL). Pyridine (7.9 mL) was added and the reaction was heated to reflux. 2-Bromomalonaldehyde (7.2 g) was added in dimethylsulfoxide (15 mL) dropwise over 10 minutes and the reaction was heated for 3 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution. The aqueous layer was back extracted and the combined organic phase was washed with brine and concentrated. The crude reaction was purified by silica gel column chromatography using an eluant of 2% to 4% acetone/dichloromethane to obtain the title compound (2.4 g) with the following physical data.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperaturethe reaction was heated for 3 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. custompartitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution
  5. extractionThe aqueous layer was back extracted
  6. washthe combined organic phase was washed with brine
  7. concentrationconcentrated
  8. customThe crude reaction
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-baf63f454415478da477e274c7e461bb
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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