Chloroacetyl chloride → HCID 67050365, compound

HRID 1878060Notes

Reaction equation

HRID 1878060 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C([N:12](CC)CC)C.[Cl:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl>[Cl:17][CH2:18][C:19]([NH:12][C:7]1[CH:2]=[N:3][CH:4]=[C:5]([C:8]#[N:9])[CH:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 8182602-Amino-5-cyanopyridine

Product 1

HCID 67050365HCID 67050365, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-amino-5-cyanopyridine (2.0 g, 16.8 mmol) in dry chloroform (40 mL) was added triethylamine (2.54 g, 25.21 mmol) with stirring at 0° C. To the reaction mixture chloroacetyl chloride (2.08 g, 18.48 mmol) was added dropwise, and stirred at 0° C. for 1 hour and then at room temperature for 12 hours. The reaction mixture was diluted with chloroform (100 mL) and washed with water (150 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was recrystallized from chloroform and petroleum ether to obtain the title compound.

Workup

  1. stirringstirred at 0° C. for 1 hour
  2. washwashed with water (150 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was recrystallized from chloroform and petroleum ether

Sources & evidence

ORD record
ord-906b197ce7f945ba9cda7e9c70151f42
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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