Hydrochloric Acid → N-(Butylcarbamoyl)-4-nitrothiophene-2-sulfonamide

HRID 434598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434598
[N+:1]([C:4]1[CH:5]=[C:6]([S:9]([NH2:12])(=[O:11])=[O:10])[S:7][CH:8]=1)([O-:3])=[O:2].[CH2:13]([N:17]=[C:18]=[O:19])[CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[CH2:13]([NH:17][C:18]([NH:12][S:9]([C:6]1[S:7][CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:10])=[O:11])=[O:19])[CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 202157164-Nitro-2-thiophenesulfonamide

Produkt 1

HCID 20215715N-(Butylcarbamoyl)-4-nitrothiophene-2-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A stirred suspension of 10 g of 4-nitrothiophene-2-sulfonamide, 6 g of n-butyl isocyanate and 7 g of anhydrous potassium carbonate in 100 ml of acetone was heated to reflux for 3 hours. The resultant viscous mixture was poured into ice-water and the pH adjusted to 2 by the addition of concentrated hydrochloric acid. The resulting tarry precipitate thus obtained was extracted into methylene chloride, separated from the aqueous phase, dried over magnesium sulfate, filtered and concentrated in-vacuo. The residue which showed absorption peaks by NMR at 0.7 to 1.7 (multiplet), consistent for butyl and at 8.3 and 8.5, consistent for the thiophene ring was used without further purification in the following example.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customThe resulting tarry precipitate thus obtained
  4. extractionwas extracted into methylene chloride
  5. customseparated from the aqueous phase
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customabsorption peaks by NMR at 0.7 to 1.7 (multiplet)

Quellen und Nachweise

ORD-Eintrag
ord-c0eca668e4754635bf9a2942cceee468
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04398939

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