Chloroform → 3-Chloro-6-(o-fluorophenyl)-1,2,4-triazine

HRID 237103Notes

Reaction equation

HRID 237103 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11](=O)[NH:12][N:13]=1.C(Cl)(Cl)[Cl:16].P(Cl)(Cl)(Cl)=O.CN(C)C=O>CCCCCC>[Cl:16][C:11]1[N:12]=[N:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 125812866-(o-fluorophenyl)-1,2,4-triazin-3(2H)-one

Product 1

HCID 213152223-Chloro-6-(o-fluorophenyl)-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A suspension of 42.4 g. of 6-(o-fluorophenyl)-1,2,4-triazin-3(2H)-one in 350 ml. of chloroform is refluxed overnight, cooled in an ice bath, and 350 ml. of phosphorus oxychloride followed by 2.6 g. of N,N-dimethylformamide are added. The mixture is refluxed for 4.5 hours, cooled and concentrated to a brown oil. This oil is dissolved in methylene chloride, poured onto ice and made basic, giving a brown solid. The mixture is filtered and the filtrate is passed through a silica gel column giving a crystalline solid. This solid is heated with hexane and filtered giving crystals. Recrystallization from hexane gives a tan solid which sublimes on heating giving 3-chloro-6-(o-fluorophenyl)-1,2,4-triazine as tan crystals.

Workup

  1. additionA suspension of 42.4 g
  2. temperaturecooled in an ice bath
  3. temperatureThe mixture is refluxed for 4.5 hours
  4. temperaturecooled
  5. concentrationconcentrated to a brown oil
  6. dissolutionThis oil is dissolved in methylene chloride
  7. additionpoured onto ice
  8. customgiving a brown solid
  9. filtrationThe mixture is filtered
  10. customgiving a crystalline solid
  11. filtrationfiltered
  12. customgiving crystals
  13. customRecrystallization from hexane
  14. customgives a tan solid which
  15. temperatureon heating

Sources & evidence

ORD record
ord-98ef7605ac974f9aba1b45a37003067e
Source dataset
uspto-grants-1979_06
Patent number
US04159375

Reaction notes

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