Potassium Carbonate → 4-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamide

HRID 46303

Reaktionsgleichung

Reaktionsgleichung von HRID 46303
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[S:21][C:20]([N:22](CC2C=CC(OC)=CC=2OC)[S:23]([C:26]2[CH:31]=[CH:30][C:29](F)=[C:28]([C:33]#[N:34])[CH:27]=2)(=[O:25])=[O:24])=[N:19][CH:18]=1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:29]2[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:20]3[S:21][C:17]([Cl:16])=[CH:18][N:19]=3)(=[O:24])=[O:25])=[CH:27][C:28]=2[C:33]#[N:34])=[C:4]([I:9])[CH:3]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6202344-Chloro-2-iodophenolHCID 59436479N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-N-(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide

Produkt 1

HCID 594364884-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of 4-chloro-2-iodophenol (305 mg, 1.20 mmol) and potassium carbonate (207 mg, 1.5 mmol) in dimethyl sulphoxide (5.0 ml) was added N-(5-chloro-1,3-thiazol-2-yl)-3-cyano-N-(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide (Preparation 207, 468 mg, 1.00 mmol). Suspension stirred at room temperature for 18 hours. The reaction mixture was poured into ethyl acetate (20 ml) and saturated aqueous ammonium chloride solution (20 ml) and the aqueous layer extracted with ethyl acetate (3×20 ml). Combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude residue was dissolved in dichloromethane (5 ml), trifluoroacetic acid (5 ml) was added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated in vacuo and purified by ISCO™ preparative system eluting with dichloromethane:ethyl acetate (gradient 1:0 to 6:4, by volume) to afford the title compound as a solid, 396 mg, 72% yield.

Aufarbeitung

  1. extractionthe aqueous layer extracted with ethyl acetate (3×20 ml)
  2. dry with materialCombined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved in dichloromethane (5 ml)
  5. additiontrifluoroacetic acid (5 ml) was added
  6. stirringthe reaction mixture was stirred at room temperature for 2 hours
  7. concentrationThe solvent was concentrated in vacuo
  8. custompurified by ISCO™ preparative system
  9. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-5bfacce7c223498393581bb4a135bd77
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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