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Hydrochloric Acid → 2-(2-(3-(Trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acid

HRID 660052
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 660052
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Cl[CH2:18][CH2:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)(=[O:22])=[O:21].Cl>CN(C=O)C.C(OCC)(=O)C.O>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([S:20]([CH2:19][CH2:18][S:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])(=[O:21])=[O:22])[CH:28]=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27365062-Chloroethyl-[3-(trifluoromethyl)phenyl]sulphoneHCID 178524460HCID 178524460, Verbindung

Produkt 1

HCID 28213922-(2-(3-(Trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acidAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

683 mg (4.92 mmol) of K2CO3 were added to a suspension of 349 mg (2.25 mmol) of 2-mercaptonicotinic acid in DMF (5 ml), and the mixture was stirred for 30 min at RT. 614 mg (2.25 mmol) of 2-chloroethyl-(3-(trifluoromethyl)phenyl)sulfone were then added, and stirring was continued for a further 72 h at RT. The reaction solution was concentrated in vacuo, the residue obtained was taken up in ethyl acetate, and water was added. The pH was adjusted to 3 with 2 M hydrochloric acid, and the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. 778 mg (1.99 mmol, 88%) of 2-(2-(3-(trifluoromethyl)phenylsulfonyl)ethylthio)nicotinic acid were obtained as residue.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further 72 h at RT
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe residue obtained
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d01fe1f38a9343b5b7ab2a489df79fba
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084470B2

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