Thiophenol → HCID 20475704, compound

HRID 905209Notes

Reaction equation

HRID 905209 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]1[N:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=1>[O-]CC.[Na+].C(O)C>[C:1]1([S:7][C:9]2[N:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7969ThiophenolHCID 5906412,5-Dichloropyrimidine

Product 1

HCID 20475704HCID 20475704, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

A solution of thiophenol (60 mmol) in 0.43 M sodium ethoxide (150 ml) and a solution of 2,5-dichloropyrimidine (60 mmol) in absolute ethanol (90 ml) were mixed and heated under reflux for 2 h. The cold mixture was then filtered, the filtrate evaporated, the residual material dissolved in chloroform (150 ml), the chloroform solution washed with 2 M NaOH (2×15 ml) and water (15 ml) and the dried (MgSO4) solution evaporated leaving an oily material which crystallized in the cold; yield 70%, m.p. 47° C. (ligroin). 1H NMR (CDCl3): δ7.4(Ph), 8.33 (H-4, H-6).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. filtrationThe cold mixture was then filtered
  4. customthe filtrate evaporated
  5. dissolutionthe residual material dissolved in chloroform (150 ml)
  6. washthe chloroform solution washed with 2 M NaOH (2×15 ml) and water (15 ml)
  7. dry with materialthe dried (MgSO4) solution
  8. customevaporated
  9. customleaving an oily material which
  10. customcrystallized in the cold

Sources & evidence

ORD record
ord-e518603840d34eeb9d7b604f89b7eee3
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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