Triethylamine → HCID 67050161, compound

HRID 1878068Notes

Reaction equation

HRID 1878068 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:17][CH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20]>ClCCl.C(Cl)(Cl)Cl>[Cl:17][CH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]([NH:1][C:2]1[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1)=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chlorideHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 67050161HCID 67050161, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-amino-2-cyanopyridine (0.500 g, 4.2 mmol) in dry dichloromethane (20 mL) was added triethylamine (0.637 g, 6.3 mmol) and the mixture was stirred at 0° C. α-Chloro phenylacetyl chloride (0.952 g, 5.04 mmol) was added dropwise to the mixture, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with chloroform (100 mL) and washed with water (150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel and ethyl acetate (20%) in petroleum ether as an eluent) to obtain the title compound.

Workup

  1. additionwas added dropwise to the mixture
  2. washwashed with water (150 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto obtain the crude product, which
  6. customwas purified by column chromatography (silica gel and ethyl acetate (20%) in petroleum ether as an eluent)

Sources & evidence

ORD record
ord-b096aaa5a1fd4594bdd80274b18765f1
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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