Hydrochloric Acid → 3,4-Dimethoxy-N-(4-(3-nitrophenyl)-2-thiazolyl)benzenesulfonamide

HRID 1417265

Reaktionsgleichung

Reaktionsgleichung von HRID 1417265
Br.[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].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([S:27](Cl)(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].Cl>N1C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([S:27]([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:28])=[O:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 28704454-(3-Nitro-phenyl)-thiazol-2-ylamine hydrobromide

Produkt 1

HCID 52823373,4-Dimethoxy-N-(4-(3-nitrophenyl)-2-thiazolyl)benzenesulfonamideAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.43 g of 3,4-dimethoxy-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 organic phase was separated and dissolved in a mixture of 20 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 as an oil upon neutralization and was thereupon treated once more with active charcoal. The product separated upon renewed neutralization with concentrated hydrochloric acid. Recrystallization from 25 ml of 60% ethanol yielded 0.12 g of 3,4-dimethoxy-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as colourless crystals.

Aufarbeitung

  1. customthe organic phase was separated
  2. dissolutiondissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  3. additionAfter the addition of 0.5 g of active charcoal the mixture
  4. filtrationsubsequently the active charcoal was filtered off
  5. customThe product separated as an oil upon neutralization
  6. additionwas thereupon treated once more with active charcoal
  7. customThe product separated
  8. customRecrystallization from 25 ml of 60% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-09b2ec246811457babc137cc80331ffe
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877193

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