Cyanogen Bromide → [(6-Chloropyridin-3-yl)methyl]cyanamide

HRID 520754Notes

Reaction equation

HRID 520754 reaction equation
[N:1]#[C:2]Br.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][N:6]=1>C(Cl)(Cl)Cl>[Cl:4][C:5]1[N:6]=[CH:7][C:8]([CH2:11][NH:12][C:2]#[N:1])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 51342138[(6-Chloropyridin-3-yl)methyl]cyanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Cyanogen bromide (220 mg, 2.09 mmol) was dissolved in 10 mL of anhydrous chloroform, and the solution was cooled to 0° C. To this was dropwise added a solution of 500 mg (3.49 mmol) of 2-chloro-5-aminomethylpyridine dissolved in 10 mL of anhydrous chloroform, and the resulting mixture was stirred at 0° C. for 1 hour. The reaction mixture was filtered, then water was added and liquid-liquid extraction was carried out, following which the chloroform phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=1:1), giving 122 mg (yield, 35%) of the target compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionwater was added
  3. extractionliquid-liquid extraction
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)
  7. customgiving
  8. custom122 mg (yield, 35%) of the target compound

Sources & evidence

ORD record
ord-dfe98bc203ff44248acc7b59710b20e9
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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