Phenylacetyl chloride → HCID 67050467, compound

HRID 1878065Notes

Reaction equation

HRID 1878065 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.[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.C(Cl)(Cl)Cl>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:24](=[O:25])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:3][CH:4]=1)#[N:9]

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 67050467HCID 67050467, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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. To the reaction mixture phenylacetyl chloride (0.973 g, 6.3 mmol) was added dropwise and stirred at 0° C. for 1 hour and then 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 using column chromatography (silica gel, 20% ethyl acetate in petroleum ether as an eluent) to obtain the title compound.

Workup

  1. stirringstirred at 0° C. for 1 hour
  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

Sources & evidence

ORD record
ord-073de9e717b644f197515fc98da01cb0
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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