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Chloroacetyl chloride → 2-chloro-N-(pyridin-2-ylmethyl)acetamide

HRID 2112396
Notes
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Reaction equation

HRID 2112396 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CC(C)=O>[Cl:15][CH2:16][C:17]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 195092-Pyridinemethanamine

Product 1

HCID 24974842-chloro-N-(pyridin-2-ylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.5 g (4.6 mmol) 2-(aminomethyl)pyridine in 10 ml acetone at 0° C. were added 1.27 g (9.2 mmol) potassium carbonate and 0.57 g (5.1 mmol) 2-chloro acetylchloride. The reaction was stirred at 0° C. until no starting material remained and then poured onto ice water. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with aqueous NaHCO3 (sat.) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used directly for the next step. MS(ISP): 185.21 ([MH]+.

Workup

  1. additionpoured onto ice water
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with aqueous NaHCO3 (sat.) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62f6afb793ad4b1d9298364b1f73f3fc
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07524823B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes