Chloroacetyl chloride → n-(5-Bromo-3-methyl-pyridin-2-yl)-2-chloro-acetamide

HRID 1916740

Reaction equation

HRID 1916740 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([Br:14])=[CH:9][N:8]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:14][C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([NH:6][C:3](=[O:4])[CH2:2][Cl:1])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 52228026n-(5-Bromo-3-methyl-pyridin-2-yl)-2-chloro-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.75 mL (22 mmol) chloroacetyl chloride are added to a solution, cooled to 0° C., of 3.74 g (20 mmol) 2-amino-5-bromo-3-methylpyridine in 50 mL DCM and then 6.1 mL (44 mmol) triethylamine are slowly added dropwise. After the addition has ended the ice bath is removed and the reaction mixture is stirred for 4 h at RT. It is poured onto water, extracted exhaustively with DCM, the combined organic phases are washed with water and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 2:1).

Workup

  1. additionAfter the addition
  2. customis removed
  3. additionIt is poured onto water
  4. extractionextracted exhaustively with DCM
  5. washthe combined organic phases are washed with water and saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customis purified by chromatography (silica gel, cyc/EtOAc 2:1)

Sources & evidence

ORD record
ord-4aede1005bfe4e03826578031574b8ca
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Linked notes

Loading…