Hydrochloric Acid → 5-tert-Butyl-thiophene-2-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide

HRID 1417266

Reaktionsgleichung

Reaktionsgleichung von HRID 1417266
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].[C:17]([C:21]1[S:25][C:24]([S:26](Cl)(=[O:28])=[O:27])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].Cl>N1C=CC=CC=1>[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH:16][S:26]([C:24]3[S:25][C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:22][CH:23]=3)(=[O:27])=[O:28])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 28704454-(3-Nitro-phenyl)-thiazol-2-ylamine hydrobromideHCID 218455645-Tert-butylthiophene-2-sulfonyl chloride

Produkt 1

HCID 867537555-tert-Butyl-thiophene-2-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide

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 5-tert-butyl-thiophene-2-sulfonyl 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 three times with 30 ml of ethyl acetate each time. The organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. The residue was chromatographed on 50 g of Kieselgel 60 with ethyl acetate/hexane (1:2) as the eluent. The product-containing fractions were concentrated and the residue was dissolved in a mixture of 20 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. 0.20 g of 5-tert-butyl-thiophene-2-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide separated as yellowish crystals after neutralization with concentrated hydrochloric acid and repeated boiling.

Aufarbeitung

  1. extractionthe mixture was extracted three times with 30 ml of ethyl acetate each time
  2. dry with materialdried with magnesium sulphate
  3. customthe solvent was removed on a rotary evaporator
  4. customThe residue was chromatographed on 50 g of Kieselgel 60 with ethyl acetate/hexane (1:2) as the eluent
  5. concentrationThe product-containing fractions were concentrated
  6. dissolutionthe residue was dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  7. additionAfter the addition of 0.4 g of active charcoal the mixture
  8. filtrationsubsequently the active charcoal was filtered off
  9. custom0.20 g of 5-tert-butyl-thiophene-2-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide separated as yellowish crystals after neutralization with concentrated hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-5cb6bbc3033443ecaef34c37ddeede3f
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877193

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