Sodium ethoxide → HCID 178517571, Verbindung

HRID 530745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530745
Cl.[F:2][C:3]([F:13])([F:12])[C:4]1[N:5]=[C:6]([C:9]([NH2:11])=[NH:10])[S:7][CH:8]=1.C([O:16][C:17]([C:19]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:20][O-])=O)C.[Na+].CC[O-].[Na+]>CCO>[O:22]([C:19]1[C:17]([OH:16])=[N:10][C:9]([C:6]2[S:7][CH:8]=[C:4]([C:3]([F:2])([F:12])[F:13])[N:5]=2)=[N:11][CH:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 66730292HCID 66730292, VerbindungHCID 667304744-(Trifluoromethyl)thiazole-2-carboximidamide hydrochloride

Produkt 1

HCID 178517571HCID 178517571, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of compound 282 (280 mg, 1 eq.) in dry EtOH (6 mL) was added compound 291 (1.38 g, 5 eq.) under nitrogen, followed by NaOEt (165 mg, 1 eq.). The reaction mixture was stirred at 90° C. for 2 hrs. EtOH was evaporated and a DCM/water mixture was added. Aqueous layer was acidified to pH 5 with aqueous 1N HCl and was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo, and purified by chromatography on silica gel (DCM/MeOH) to yield compound AI1 as a beige oil in 81% yield. MS (ESI, EI+): m/z=340 (MH+).

Aufarbeitung

  1. customEtOH was evaporated
  2. additiona DCM/water mixture was added
  3. extractionwas extracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography on silica gel (DCM/MeOH)
  8. customto yield compound AI1 as a beige oil in 81% yield

Quellen und Nachweise

ORD-Eintrag
ord-fa960f2374e34d63ab3cfd519ca9e431
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353100B2

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