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

HRID 252213

Reaction equation

HRID 252213 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-21080ef525f644fe89e30e080a0f2842
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Linked notes

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