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

HRID 81704

Reaction equation

HRID 81704 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-98a58531368e4b3a9fc71ff718e59e4b
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Linked notes

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