Dimethylformamide → HCID 89854217, compound

HRID 931127Notes

Reaction equation

HRID 931127 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1)#[N:14]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 467389795-Bromo-N-methylpyridine-3-sulfonamide

Product 1

HCID 89854217HCID 89854217, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N-methylpyridine-3-sulfonamide (0.1 g, 0.39 mmol) in N,N-dimethylformamide was added zinc cyanide (0.056 g, 0.47 mmol). The solution was degassed with nitrogen for 10 min, then tetrakis(triphenylphosphine)palladium(0) (30 mg) was added. The reaction mixture was heated to 100° C. for 2 h. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was dried, filtered, and concentrated under reduced pressure. The crude compound was purified by rinsing with diethyl ether to afford 5-cyano-N-methylpyridine-3-sulfonamide (60 mg) which was used without further purification.

Workup

  1. customThe solution was degassed with nitrogen for 10 min
  2. additiontetrakis(triphenylphosphine)palladium(0) (30 mg) was added
  3. additionThe mixture was then diluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified
  9. washby rinsing with diethyl ether

Sources & evidence

ORD record
ord-9f254e608b4342e2ab6a2f1954aaf2cc
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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