Hydrochloric Acid → N-(3-Pyrrolidin-3-yl-phenyl)-3-trifluoromethoxy-benzenesulfonamide

HRID 238968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238968
COC([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=3)(=[O:19])=[O:18])[CH:11]=2)[CH2:6]1)=O.Cl>C(O)C>[NH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:28])[F:29])[CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH2:6]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 689511843-[3-(3-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester

Produkt 1

HCID 68949003N-(3-Pyrrolidin-3-yl-phenyl)-3-trifluoromethoxy-benzenesulfonamideAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-[3-(3-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester (0.105 g; 0.24 mmol) were dissolved in 2.5 ml ethanol and 0.9 ml of concentrated HCl were added. The reaction mixture was heated in a microwave system (CEM) at 90-150° C. for several hours until consumption of starting material. The mixture was then concentrated in vacuo and the acidic aqueous phase extracted twice with diethylether. The aqueous phase was adjusted to pH 9 with 1 N aqueous NaOH, extracted three times with diethylether, and the combined organic layers dried over sodium sulfate, filtered and the solvent evaporated to dryness to yield 45 mg of the product.

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionthe acidic aqueous phase extracted twice with diethylether
  3. extractionextracted three times with diethylether
  4. dry with materialthe combined organic layers dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bf39860572d5441ab6a39daa997349a0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642642B2

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