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

HRID 252213

反応式

HRID 252213 の反応式
[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

5

反応物 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 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.

後処理

  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

出典と根拠

ORDレコード
ord-21080ef525f644fe89e30e080a0f2842
出典データセット
uspto-grants-2011_01
特許番号
US07868026B2

関連ノート

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