Hydrochloric Acid → 2-Ethyl-3-(4-chloro-3-sulfamoylbenzoyl)-benzo[b]furan

HRID 263284

Reaktionsgleichung

Reaktionsgleichung von HRID 263284
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].ClC1C=CC(C(O)=O)=CC=1S(=O)(=O)N.S(Cl)(Cl)=O.[CH2:33]([C:35]1[O:39][C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[CH:36]=1)[CH3:34].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[CH2:33]([C:35]1[O:39][C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[C:36]=1[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:4]=1)[CH3:34]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 24386Thionyl ChlorideHCID 765822-EthylbenzofuranHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 213165862-Ethyl-3-(4-chloro-3-sulfamoylbenzoyl)-benzo[b]furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

10 mg of powdered 4-chloro-3-sulfamoylbenzoyl chloride (melting point, m.p. 166° C.), prepared from 4-chloro-3-sulfamoylbenzoic acid and thionyl chloride, are introduced into 70 ml of anhydrous chlorobenzene, subsequently 6.32 g of 2-ethylbenzo[b]furan are added, and the reaction mixture is cooled to 0° C. After addition of 11.4 g of anhydrous aluminum chloride, the reaction batch is maintained at a temperature of 5° to 10° C., subsequently stirred for 5 hours at 15° C., and the mixture is then poured into a suspension of 200 g of ice and 10 ml of concentrated hydrochloric acid. After extraction with ethyl acetate and washing with water, the organic phase is stirred for 6 hours with a dilute NaHCO3 solution having a pH of 8.5, dried over magnesium sulfate, and, after evaporation, a light yellow to colorless viscous oil is obtained which crystallizes from petroleum ether. Colorless crystals, m.p. 170°-172° C. (from a small amount of methanol).

Aufarbeitung

  1. additionare added
  2. temperaturethe reaction batch is maintained at a temperature of 5° to 10° C.
  3. extractionAfter extraction with ethyl acetate
  4. washwashing with water
  5. stirringthe organic phase is stirred for 6 hours with a dilute NaHCO3 solution
  6. dry with materialdried over magnesium sulfate
  7. customafter evaporation
  8. customa light yellow to colorless viscous oil is obtained which
  9. customcrystallizes from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9b94943a4cff48128432d38db0f93c8b
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156732

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