Hydrochloric Acid → N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-4-methoxy-benzenesulfonamide

HRID 1417285

Reaktionsgleichung

Reaktionsgleichung von HRID 1417285
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.Cl>N1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:12])[F:11])=[CH:5][C:4]=1[C:13]1[N:14]=[C:15]([NH:18][S:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=2)(=[O:29])=[O:28])[S:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 218455954-(2-Fluoro-5-trifluoromethyl-phenyl)-thiazol-2-ylamine hydrobromide

Produkt 1

HCID 21845573N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-4-methoxy-benzenesulfonamideAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g of 4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-ylamine hydrobromide with 0.33 g of 4-methoxy-benzenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated. The residue was dissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 30 ml of 50% ethanol yielded 0.26 g of N-[4-(2-fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-4-methoxy-benzenesulfonamide as colorless crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 0.5 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated upon neutralization with concentrated hydrochloric acid
  8. customRecrystallization from 30 ml of 50% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-613a7b7d95e94a6283c4227301cb3418
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877193

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