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

HRID 577393
Notes
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Reaction equation

HRID 577393 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×
HCID 962
Water
Solvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-834b7b4417d94d2a9392c631174c02fd
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040549B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes