Methanol → N-(tert-Butyl)-1H-pyrrole-3-sulfonamide

HRID 1844743

Reaktionsgleichung

Reaktionsgleichung von HRID 1844743
[C:1]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC(O)=O>[C:1]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 86719139N-(tert-Butyl)-1-tosyl-1H-pyrrole-3-sulfonamide

Produkt 1

HCID 19693846N-(tert-Butyl)-1H-pyrrole-3-sulfonamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of compound 27c (665 mg, 1.87 mmol) in a mixture of THF (12 mL), MeOH (12 mL) and water (3 mL) was added K2CO3 (3.1 g, 22 mmol) and then the solution was heated at 60° C. overnight, cooled, acidified to pH=5 with AcOH and extracted with EA twice. The combined organic layers were washed with water (3×) and brine, concentrated and purified by CC (PE/EA=2/1) to give compound 27d (260 mg, 69%) as a solid.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with EA twice
  3. washThe combined organic layers were washed with water (3×) and brine
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-23659cd8d00544bf89aaaa18cadb6b73
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946446B2

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