Acetonitrile → Methyl 2-(pyridin-3-ylmethylthio)benzoate

HRID 252213

Reaktionsgleichung

Reaktionsgleichung von HRID 252213
[SH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:13][C:14]1[CH:19]=C[CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CC#[N:28]>>[N:28]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:13][S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:19]=1

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl ester

Produkt 1

HCID 58924355Methyl 2-(pyridin-3-ylmethylthio)benzoate

Versuchsvorschrift

A mixture of compound 2 (70.0 g, 0.4167 mol), 1-(bromomethyl)benzene (82.8 g, 0.5 mol), K2CO3 (350 g, 2.49 mol) and CH3CN (500 mL) was refluxed overnight. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure. After addition of water, the mixture was extracted with CH2Cl2 (3×500 mL). The organic layers were combined, washed with aq. Na2CO3 (2×200 mL), water (2×300 mL), brine (300 mL) and dried over Na2SO4. After evaporation, crude compound 3 was obtained (64.0 g, 59.4%). This was used without further purification.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionAfter addition of water
  5. extractionthe mixture was extracted with CH2Cl2 (3×500 mL)
  6. washwashed with aq. Na2CO3 (2×200 mL), water (2×300 mL), brine (300 mL)
  7. dry with materialdried over Na2SO4
  8. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-21080ef525f644fe89e30e080a0f2842
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868026B2

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