Hydrochloric Acid → 3-cyano-4-(2-iodo-phenoxy)-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamide

HRID 46283

Reaktionsgleichung

Reaktionsgleichung von HRID 46283
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[C:15]([C:17]1[CH:18]=[C:19]([S:24]([NH:27][C:28]2[S:32][N:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1F)#[N:16].Cl>CN(C=O)C>[C:15]([C:17]1[CH:18]=[C:19]([S:24]([NH:27][C:28]2[S:32][N:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])#[N:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 107842-IodophenolHCID 11430Potassium CarbonateHCID 580423023-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Produkt 1

HCID 594366353-cyano-4-(2-iodo-phenoxy)-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamideAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-iodophenol (6.0 mmol, 1320 mg) and K2CO3 (10.5 mmol, 1450 mg) in DMF (15.0 mL) was added 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 65, 4.5 mmol, 1280 mg). The reaction mixture was heated at 80° C. for 24 hours. The reaction was cooled to room temperature and the mixture was poured into 1 N aqueous HCl (100 mL) to obtain a white solid. The afforded solid was washed with heptane and the solid was dried in vacuo to furnish 1.932 g of the title compound. LCMS Rt=1.67 minutes MS m/z 485 [MH]+

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. customto obtain a white solid
  3. washThe afforded solid was washed with heptane
  4. customthe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d03a31da76ca4ebf9a89d430e4f66cd3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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