Thiophenol → 2-Chloro-4-(phenylthio)pyrimidine

HRID 577392

Reaction equation

HRID 577392 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Na].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([S:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 775312,4-DichloropyrimidineHCID 5360545Sodium

Product 1

HCID 219952052-Chloro-4-(phenylthio)pyrimidineYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2,4-dichloropyrimidine (1.00 g, 6.71 mmol) in absolute ethanol (10 mL), was added sodium salt of benzenethiol (0.89 g, 6.73 mmol)in small portions. The mixture was stirred at room temperature for 2 hours, then at 40° C. for 16 hours. It was diluted with ethyl acetate (20 mL), and filtered. The filtrate was concentrated in vacuo, and the residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (1:99→25:75) as eluant to give the desired product (498 mg, 36%).

Workup

  1. waitat 40° C. for 16 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-3ed04ce3ef9b4af6adf98607be7aa7e5
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Linked notes

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