Sodium Hydroxide → Methyl 4-(2-chloropyrimidin-4-ylthio)benzoate

HRID 81705

Reaktionsgleichung

Reaktionsgleichung von HRID 81705
[OH-].[Na+].[SH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1>CO.O>[Cl:14][C:15]1[N:20]=[C:19]([S:3][C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)[CH:18]=[CH:17][N:16]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 775312,4-DichloropyrimidineHCID 237573Methyl 4-sulfanylbenzoate

Produkt 1

HCID 86645567Methyl 4-(2-chloropyrimidin-4-ylthio)benzoateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a sodium hydroxide (2.38 g, 59 mmol) solution in methanol (50 mL) and water (5 mL), was added dropwise a solution of methyl 4-mercaptobenzoate (9.00 g, 54 mmol) in methanol (100 mL). The mixture was stirred at room temperature for 1 hour, to this was added methanol solution (100 mL) of 2,4-dichloropyrimidine (8.77 g, 59 mmol) over 5 minutes. The whole was stirred at room temperature for 16 hours. Methanol was removed in vacuo, and the residue was partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was separated and dried (Na2SO4). Removal of the solvent in vacuo yielded the product (14.60 g, 97%).

Aufarbeitung

  1. stirringThe whole was stirred at room temperature for 16 hours
  2. customMethanol was removed in vacuo
  3. customthe residue was partitioned between ethyl acetate (200 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-83b45eba4ee148e4b7259d52a21eb72b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846704B2

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