Chloroacetyl chloride → 2-Chloro-N-pyridin-2-yl-acetamide

HRID 897

Reaction equation

HRID 897 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 104392-AminopyridineHCID 81531Diisopropylethylamine

Product 1

HCID 2894352-Chloro-N-pyridin-2-yl-acetamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetylchloride (60 g, 0.53M) was added with stirring to a mixture of 2-aminopyridine (50 g, 0.53M) and diisopropylethylamine (75 ml, 0.53M) in dichloromethane (500 ml) keeping the temperature below 5° C. After the reaction mixture was warmed to room temperature it was filtered and washed with water. The organic layer was dried (MgSO4) and evaporated under reduced pressure to give 72.6 g of a brown solid.

Workup

  1. customthe temperature below 5° C
  2. filtrationwas filtered
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3287b7f0e07644e393371b77d33adaf0
Source dataset
uspto-grants-1998_03
Patent number
US05723464

Linked notes

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