Dimethylformamide → 3-Chloro-6-phenyl-1,2,4-triazine

HRID 2245931Notes

Reaction equation

HRID 2245931 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10](=O)[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:10]1[N:11]=[N:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 112637836-Phenyl-1,2,4-triazin-3(2H)-one

Product 1

HCID 110306323-Chloro-6-phenyl-1,2,4-triazineYield 81.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-phenyl-1,2,4-triazin-3(2H)-one (2.45 g, 0.0141 mol) and DMF (0.5 mL) in phosphoryl chloride (20.0 mL, 0.214 mol) and chloroform (20.0 mL) was heated under reflux overnight. After cooling, the volatiles were removed under reduced pressure. The residue was dissolved in DCM (60 mL) and was poured into ice with stirring. The mixture was neutralized with NaOH (1N), and filtered through a pad of celite to remove a small amount of insoluble residue. The organic layer was separated. The aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (2.20 g, 81.1%). Analytical LCMS: (M+H)+=192.1/194.1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customthe volatiles were removed under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (60 mL)
  6. additionwas poured into ice
  7. filtrationfiltered through a pad of celite
  8. customto remove a small amount of insoluble residue
  9. customThe organic layer was separated
  10. extractionThe aqueous layer was extracted with DCM (3×20 mL)
  11. dry with materialThe combined organic layers were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-92de6bbfb0ab43099212a30af1dcb3cd
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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