Cyanogen Bromide → HCID 15650344, compound

HRID 465992Notes

Reaction equation

HRID 465992 reaction equation
[Br-].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:16]#[C:17]Br>CCOCC>[CH2:9]([N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]1=[N:2][C:17]#[N:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 12255191HCID 12255191, compound

Product 1

HCID 15650344HCID 15650344, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.3 g (20 mmole) of 2-amino-1-benzylpyridinium bromide [prepared according to Chem. Ber. 88, 1103 (1955)] are suspended in 20 ml of ether, then 20 ml of aqueous sodium hydroxide solution of 0.5 mole/liter concentration are added while stirring. After the dissolution of the solid phase the phases are separated and the aqueous phase is extracted with 20 ml of ether. The combined organic phase is dried over anhydrous sodium sulfate and evaporated to its half volume under reduced pressure. Then, a solution containing 1.1 g (10 mmole) of cyanogen bromide in 5 ml of ether is dropped to the ethereal solution at room temperature under stirring. After stirring for 30 minutes the crystalline precipitate is filtered, washed with ether and then with a great volume of water, then the product is dried in air to yield 0.91 g (44%) of the named product, m.p.: 139°-140° C. (after recrystallization from ethanol the melting point raises to 147°-148° C.). On the basis of its melting point, infrared spectrum and thin layer chromatography (TLC) characteristics, this product proved to be indentical to the target compound of Example 2.

Workup

  1. concentration20 ml of aqueous sodium hydroxide solution of 0.5 mole/liter concentration
  2. additionare added
  3. dissolutionAfter the dissolution of the solid phase the phases
  4. customare separated
  5. extractionthe aqueous phase is extracted with 20 ml of ether
  6. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  7. customevaporated to its half volume under reduced pressure
  8. additionis dropped to the ethereal solution at room temperature
  9. stirringunder stirring
  10. stirringAfter stirring for 30 minutes the crystalline precipitate
  11. filtrationis filtered
  12. washwashed with ether
  13. dry with materialwith a great volume of water, then the product is dried in air

Sources & evidence

ORD record
ord-4a080cf14bfb4eed9fc9358dc37c2db2
Source dataset
uspto-grants-1992_10
Patent number
US05155123

Reaction notes

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