Chloroacetyl chloride → 2-chloro-N-(5-cyano-2-pyridinyl)acetamide

HRID 2192380Notes

Reaction equation

HRID 2192380 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:17][CH2:18][C:19](Cl)=[O:20]>ClCCl>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1)=[O:20]

Participants

5

Reactant 3

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

Product 1

HCID 445742932-chloro-N-(5-cyano-2-pyridinyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-5-cyano pyridine (2.0 g) in dry dichloromethane (17 mL) under nitrogen at 0° C. was treated with triethylamine (2.6 mL) followed by slow addition of chloroacetyl chloride (1.5 mL). The reaction mixture was allowed to warm up to room temperature. After 2 h, the mixture was partitioned between dichloromethane and water. The phases were separated and the aqueous layer was extracted with dichloromethane (×2). The combined organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated to give the crude product which was purified by silica gel chromatography eluting with 50% EtOAc/cyclohexane. The relevant fractions were combined and evaporated to give the title compound (2.17 g) as a light brown solid.

Workup

  1. customthe mixture was partitioned between dichloromethane and water
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by silica gel chromatography
  10. washeluting with 50% EtOAc/cyclohexane
  11. customevaporated

Sources & evidence

ORD record
ord-c1340487fdf44dea97cee85613923909
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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