Potassium Iodide → Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate

HRID 1655891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655891
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Br[CH2:19][C:20]#[N:21].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O>[C:20]([CH2:19][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1=[O:1])#[N:21]

Komponenten

7

Edukt 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 2778792Ethyl 2-(3-oxo-3,4-dihydro-2h-1,4-benzothiazin-2-yl)acetate

Produkt 1

HCID 10062806Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetateAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

After 1.82 g of ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate, 1.31 g of bromoacetonitrile and 146 mg of potassium iodide were dissolved in dimethylsulfoxide (18 ml), 1.50 g of potassium carbonate was added to the solution. The mixture was stirred at room temperature for 40 hours. After saturated ammonium chloride aqueous solution was added to the reaction mixture, the mixture was extracted with ethyl acetate. After the organic phase was washed with saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting semicrystalline residue was dissolved in benzene. After insoluble matters were filtered off, the solvent was distilled off. Isopropyl ether was added to the residue for crystallization to give 1.74 g of the title compound. The structural formula and physical data of this compound are shown in Table 5.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter the organic phase was washed with saturated sodium chloride aqueous solution
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. dissolutionThe resulting semicrystalline residue was dissolved in benzene
  6. filtrationAfter insoluble matters were filtered off
  7. distillationthe solvent was distilled off
  8. additionIsopropyl ether was added to the residue for crystallization

Quellen und Nachweise

ORD-Eintrag
ord-6063f0cf426240e584fe1b27bf8da548
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05252571

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