Water → HCID 10737609, Verbindung

HRID 2292917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292917
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:16].O>CN(C)C(=O)C>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:19][C:18]=1[S:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)#[N:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 10585340HCID 10585340, Verbindung

Produkt 1

HCID 10737609HCID 10737609, VerbindungAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.62 g 10.2 mmol) in N,N-dimethylacetamide (15 mL) was rapidly added thionyl chloride (1.30 g, 10.9 mmol) and the mixture (a precipitate formed after a few minutes) stirred at -20° C. to -5° C. for 1 hour. 4-Cyano-3-phenylthiobenzenamine (1.55 g, 6.85 mmol) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into water, extracted with ethyl ether (2×100 mL); the ethereal extracts dried (MgSO4), filtered and the solvent removed in vacuo. The residue was chromatographed on 315 g of silica gel using a ethyl ether (0%, 10%, and 20%) in methylene chloride gradient. The proper fractions were combined, the solvent removed in vacuo and the residue dissolved in a mixture of 100 mL hexane and 150 mL methylene chloride. Most of the methylene chloride was distilled off as the solution was scratched to induce crystal growth. After cooling the solid was collected and dried at 85° C./0.1 mm to yield the title propanamide (2.38 g, 91%); mp 111°-113° C.

Aufarbeitung

  1. customthe mixture (a precipitate formed after a few minutes)
  2. stirringto stir at room temperature overnight
  3. extractionextracted with ethyl ether (2×100 mL)
  4. dry with materialthe ethereal extracts dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed on 315 g of silica gel using a ethyl ether (0%, 10%, and 20%) in methylene chloride gradient
  8. customthe solvent removed in vacuo
  9. dissolutionthe residue dissolved in a mixture of 100 mL hexane and 150 mL methylene chloride
  10. distillationMost of the methylene chloride was distilled off as the solution
  11. temperatureAfter cooling the solid
  12. customwas collected
  13. customdried at 85° C./0.1 mm

Quellen und Nachweise

ORD-Eintrag
ord-f0dbd75f46d44eed94c3bea6e3ff5f95
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684198

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