Water → HCID 86657123, compound

HRID 2383333Notes

Reaction equation

HRID 2383333 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]#[N:13])[CH:3]=1.C(N)(=[S:16])C.O>CN(C)C=O.O1CCOCC1.Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12](=[S:16])[NH2:13])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2723949ThioacetamideHCID 534856984-Bromonaphthalene-2-carbonitrile

Product 1

HCID 86657123HCID 86657123, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromonaphthalene-2-carbonitrile (0.57 g) in N,N-dimethylformamide (4 mL) and 4 mol/L HCl 1,4-dioxane solution (4 mL) was added thioacetamide (1.1 g) at room temperature, and the reaction mixture was stirred at 70° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel to give 4-bromonaphthalene-2-carbothioamide (0.48 g). To a suspension of this compound (0.48 g) in ethanol (6 mL) was added ethyl 2-chloro-acetoacetate (0.59 g), and the mixture was stirred at 65° C. for 24 hours. After cooling to room temperature, the precipitated solid was collected by filtration, washed with ethanol, and dried to give the title compound (0.41 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-099831511dcb499585696326a2323713
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

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