Hydrochloric Acid → 4-Methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 619026

Reaktionsgleichung

Reaktionsgleichung von HRID 619026
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=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:7]3[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=3)[N:12]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 218455864-(3-Nitrophenyl)thiazol-2-amine hydrochloride

Produkt 1

HCID 42339694-Methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrochloride with 0.42 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 50 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and dissolved in a mixture of 10 ml of ethanol and 10 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. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 40 ml of 50% ethanol yielded 0.35 g of 4-methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellowish crystals.

Aufarbeitung

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in a mixture of 10 ml of ethanol and 10 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.4 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. customThe product separated upon neutralization with concentrated hydrochloric acid
  7. customRecrystallization from 40 ml of 50% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a75d126499b84677b8c1bf97fe50418e
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958910

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