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

反応式

[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

参加物

反応物 4

HCID 6342Acetonitrile

HCID 7498Benzyl Bromide

HCID 11430Potassium Carbonate

HCID 21009Benzoic acid, 2-mercapto-, methyl ester

生成物 1

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

実験手順

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.