Hydrochloric Acid → HCID 59496108, compound

HRID 1513341Notes

Reaction equation

HRID 1513341 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:13]1[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:14]1)(=O)C.N1C=CC=CC=1.Cl.O>O1CCOCC1>[C:21]1([C:15]2[C:16](=[O:20])[N:17]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:18](=[O:19])[NH:13][N:14]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 59496098HCID 59496098, compound

Product 1

HCID 59496108HCID 59496108, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzoyl chloride (0.253 ml, 2.180 mmol) was added to a solution of 2-acetyl-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione (420 mg, 1.817 mmol) and pyridine (0.441 ml, 5.45 mmol) in 1,4-Dioxane (5 ml) at 5° C. Mixture was stirred at r.t. overnight. Solids were filtered off and rinsed with DCM, solvent was concentrated under reduced pressure. Residue was diluted in ethanol (20 ml), hydrochloric acid 37% in water (0.250 ml, 3.04 mmol) was added and mixture heated at 90° C. for 3 h. Solvent was concentrated and residue purified on biotage 25M silica cartridge, eluting with Cy/AcOEt 8:2 to AcOEt 100%, to give 87 mg of title compound (16% yield).

Workup

  1. filtrationSolids were filtered off
  2. washrinsed with DCM, solvent
  3. concentrationwas concentrated under reduced pressure
  4. additionResidue was diluted in ethanol (20 ml)
  5. temperaturemixture heated at 90° C. for 3 h
  6. concentrationSolvent was concentrated
  7. customresidue purified on biotage 25M silica cartridge
  8. washeluting with Cy/AcOEt 8:2 to AcOEt 100%

Sources & evidence

ORD record
ord-3717e946e0dd4f0884b321665d19f535
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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