Pyridine → N-(2-thienylcyanomethyl)-2-chloroisonicotinamide

HRID 1381982Notes

Reaction equation

HRID 1381982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](Cl)=[O:6].[NH2:11][CH:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[C:13]#[N:14].N1C=CC=CC=1>C1(C)C=CC=CC=1>[S:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[CH:12]([C:13]#[N:14])[NH:11][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 11344054HCID 11344054, compound

Product 1

HCID 14253457N-(2-thienylcyanomethyl)-2-chloroisonicotinamideYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 g (0.017 mol) of 2-chloroisonicotinoyl chloride was added dropwise to a solution of 2.8 g (0.02 mol) of 2-amino-2-(2-thienyl)acetonitrile and 1.6 g (0.02 mol) of pyridine in 30 ml of toluene while the temperature was kept at 10° to 15° C. The mixture was stirred at room temperature for 1 h. A saturated aqueous common salt solution was added thereto. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the crude product was purified according to silica gel column chromatography to obtain 1.5 g (yield: 31.8%) of light brown crystals having a melting point of 123° to 125° C.

Workup

  1. customwas kept at 10° to 15° C
  2. additionA saturated aqueous common salt solution was added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe crude product was purified
  7. customto obtain 1.5 g (yield: 31.8%) of light brown crystals

Sources & evidence

ORD record
ord-9c4cc4aa59bd4091b7b6673d734ef464
Source dataset
uspto-grants-1989_02
Patent number
US04804762

Reaction notes

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