Water → HCID 21071273, compound

HRID 1371545Notes

Reaction equation

HRID 1371545 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.C(N(CC)CC)C.[Cl:17][CH:18]([Cl:22])[C:19](Cl)=[O:20].O>ClCCl.C(OCC)(=O)C>[Cl:17][CH:18]([Cl:22])[C:19]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1)=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 210712745-Ethynylpyridin-3-amine

Product 1

HCID 21071273HCID 21071273, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-5-ethynylpyridine (20.73 g, 23.1 mmol) and triethylamine (3.54 mL, 25.42 mmol) in dichloromethane was cooled in an ice bath. A solution of dichloroacetyl chloride (2.57 mL, 25.42 mmol) in dichloromethane was added dropwise. After stirring for one more hour, water and ethyl acetate were added. The organic layer was separated, washed with saturated sodium hydrogen carbonate, dried over sodium sulfate, filtered and concentrated in vacuo to yield 3-(2,2-dichloroacetamido)-5-ethynylpyridine (3.5 g).

Workup

  1. temperaturewas cooled in an ice bath
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af35d5062ca645bd949161d4aef4719f
Source dataset
uspto-grants-2007_01
Patent number
US07157473B2

Reaction notes

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