Dimethylformamide → HCID 86720752, compound

HRID 2167700Notes

Reaction equation

HRID 2167700 reaction equation
CN(C)C=O.Cl[CH2:7][C:8]([C:10]1[N:11]=[CH:12][S:13][CH:14]=1)=O.[C:15]([CH2:17][C:18](=[S:20])[NH2:19])#[N:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[S:20]1[CH:7]=[C:8]([C:10]2[N:11]=[CH:12][S:13][CH:14]=2)[N:19]=[C:18]1[CH2:17][C:15]#[N:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14162772-CyanoethanethioamideHCID 20253614Ethanone, 2-chloro-1-(4-thiazolyl)- (9CI)

Product 1

HCID 86720752HCID 86720752, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A N,N-dimethylformamide (49 mL) suspension of 2-chloro-1-(1,3-thiazol-4-yl)ethanone (4.9 g), 2-cyanoethanethioamide (3.3 g) and potassium carbonate (4.6 g) was stirred at 60° C. for 1 hour in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. An organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1). Isopropyl ether was added to the residue, and the solid was collected by filtration to obtain the title compound (2.8 g) as a faint orange solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customAn organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)
  6. additionIsopropyl ether was added to the residue
  7. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-e8a156e2aabc4e5aa4c873be5f0805af
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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