Acetic Acid → HCID 57431053, compound

HRID 1929529Notes

Reaction equation

HRID 1929529 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[CH2:8][CH3:9].[CH3:11]C(O)=O.S(=O)(=O)(O)O.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[OH-].[NH4+]>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:10])=[C:6]([CH3:11])[C:7]=1[CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 62648Ammonium PersulfateHCID 140241633,6-Dichloro-4-ethylpyridazine

Product 1

HCID 57431053HCID 57431053, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Conditions

Temperature
72.5 °C

Procedure

To a suspension of 3,6-dichloro-4-ethylpyridazine (1 eq), AgNO3 (0.7 eq) and AcOH (2.8 eq) in H2O (9.4 mL, 0.6M) was added a solution of cone, sulfuric acid (6.6 eq) in H2O (9.4 mL, 0.6 M) at 50° C., followed by addition of a solution ammonium peroxodisulfate (5.4 eq) in H2O (9.4 mL, 0.6 M) at 60° C. for 20 min. The reaction mixture was heated at 70-75° C. for 30 min. After cooling, the reaction mixture was adjusted to pH 7 with a 25% ammonium hydroxide solution, and extracted with Et2O. The extracts were washed with H2O and dried (Na2SO4) and solvent was removed under high vacuum. The residue was purified by silica gel chromatography, eluting with 9:1 petroleum ether:EtOAc, to afford the desired product as colourless crystals. 1H NMR (400 MHz, CDCl3) δ: 2.85 (2H, q, J=7.6 Hz), 2.45 (3H, s), 1.21 (3H, t, J=7.6 Hz).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with Et2O
  3. washThe extracts were washed with H2O
  4. dry with materialdried (Na2SO4) and solvent
  5. customwas removed under high vacuum
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 9:1 petroleum ether

Sources & evidence

ORD record
ord-42e50060e5f54bde8ccd8662e41d3f3e
Source dataset
uspto-grants-2012_05
Patent number
US08188084B2

Reaction notes

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