Hydrochloric Acid → 4-Methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 619048

Reaktionsgleichung

Reaktionsgleichung von HRID 619048
Br.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)([O-:4])=[O:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>N1C=CC=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:16][C:13]2[S:14][CH:15]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N+:2]([O-:4])=[O:3])[N:12]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 218455924-(2-Nitro-phenyl)-thiazol-2-ylamine hydrobromide

Produkt 1

HCID 218455994-Methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g of 4-(2-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.47 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 30 ml of 1N hydrochloric acid and extracted twice with 40 ml of ethyl acetate each time. The organic extracts were combined, 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 0.4 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. After neutralization with concentrated hydrochloric acid and boiling there separated, upon cooling, 0.58 g of 4-methyl-N-[4-(2-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellow crystals.

Aufarbeitung

  1. extractionextracted twice with 40 ml of ethyl acetate each time
  2. dry with materialdried 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 0.4 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customAfter neutralization with concentrated hydrochloric acid and boiling there separated
  8. temperatureupon cooling

Quellen und Nachweise

ORD-Eintrag
ord-bdbb5136a3e34777ad1ab2c24e62bb15
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958910

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