Sodium Acetate → N-(5-chloropyridin-2-yl)-2-acetoxyacetamide

HRID 1820934Notes

Reaction equation

HRID 1820934 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1)=[O:4].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][O:16][C:13](=[O:15])[CH3:14])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 51511482-chloro-N-(5-chloropyridin-2-yl)acetamide

Product 1

HCID 23062652N-(5-chloropyridin-2-yl)-2-acetoxyacetamideYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-N-(5-chloropyridin-2-yl)acetamide (30.68 g) obtained in Reference Example 26(1) is dissolved in N,N-dimethylformamide (500 ml), thereto is added sodium acetate (24.55 g), and the mixture is stirred at 60° C. for 5 hours. The reaction solution is diluted with ethyl acetate, washed successively with water and saturated brine. The solution is dried over magnesium sulfate, treated with activated charcoal, and the filtrate is concentrated under reduced pressure. The resulting residue is suspended in n-hexane and crystals are collected by filtration, washed with n-hexane, and dried to give N-(5-chloropyridin-2-yl)-2-acetoxyacetamide (30.58 g). APCI-MS M/Z:229/231[M+H]+

Workup

  1. washwashed successively with water and saturated brine
  2. dry with materialThe solution is dried over magnesium sulfate
  3. additiontreated with activated charcoal
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. filtrationcrystals are collected by filtration
  6. washwashed with n-hexane
  7. customdried

Sources & evidence

ORD record
ord-69929170c9814fa581953b4d1a5fee46
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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