Thiophenol → HCID 20475735, compound

HRID 905225Notes

Reaction equation

HRID 905225 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC[O-].[Na+]>C(O)C>[C:9]1([S:15][C:2]2[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 5834662-Chloro-5-fluoropyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 20475735HCID 20475735, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-chloro-5-fluoropyrimidine (10 mmol) in ethanol (15 ml) was added dropwise over 5 min to a solution prepared from thiophenol (10 mmol) and 0.43 M NaOEt in ethanol (25 ml). Subsequently the mixture was heated to boiling and refluxed for 2 hours, filtered hot, the filtrate evaporated, the residue extracted with chloroform (50 ml), the chloroform solution shaken with 2 M NaOH (2×10 ml), then shaken with water (10 ml) and the solution evaporated; yield 69%. 1H NHR (CDCl3): δ7.4 (Pyr), 8.23 (H-4, H-6).

Workup

  1. temperatureSubsequently the mixture was heated
  2. temperaturerefluxed for 2 hours
  3. filtrationfiltered hot
  4. customthe filtrate evaporated
  5. extractionthe residue extracted with chloroform (50 ml)
  6. stirringshaken with water (10 ml)
  7. customthe solution evaporated

Sources & evidence

ORD record
ord-ba5dbe43f4154eefa7f31eca51e333fb
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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