Methanol → 1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde

HRID 252005Notes

Reaction equation

HRID 252005 reaction equation
CO.[Cl:3][C:4]1[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[CH:15]=[O:16])=[N:6][CH:7]=[CH:8][CH:9]=1.[S-:17][C:18]#[N:19].[Na+].BrBr>[Br-].[Na+].CO>[Cl:3][C:4]1[C:5]([N:10]2[C:14]([S:17][C:18]#[N:19])=[CH:13][CH:12]=[C:11]2[CH:15]=[O:16])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24408BromineHCID 516871Sodium thiocyanateHCID 587620783-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

Product 1

HCID 866325621-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehydeYield 125.4%

Reagents, catalysts & solvents 1

HCID 20267117Sodium bromide methanolSolvent

Procedure

To 10 ml of methanol were added 1.0 g of 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine and 1.4 g of sodium thiocyanate. A solution of 1.0 g of bromine in 5 ml of saturated sodium bromide-methanol was added dropwise thereto at −20° C. The resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was added to 100 ml of ice water, and extracted with chloroform two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.6 g of 1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. customat −20° C
  2. extractionextracted with chloroform two times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04403b1700a844b48fe01341652056e6
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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