Sulfuric Acid → HCID 15851832, compound

HRID 1366861Notes

Reaction equation

HRID 1366861 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[C:9](O)(=O)[CH2:10][CH2:11][CH2:12]C.S(=O)(=O)(O)O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[OH-].[NH4+]>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][C:7]=1[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7991Pentanoic AcidHCID 14923Ammonium HydroxideHCID 62648Ammonium PersulfateHCID 673313,6-Dichloropyridazine

Product 1

HCID 15851832HCID 15851832, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Procedure

To a stirred suspension of 3,6-dichloropyridazine (22.5 g, 0.151 mol), silver nitrate (12.7 g, 0.074 mol) and valeric acid (20.0 g, 0.195 mol) in water (250 ml) was added a solution of sulfuric acid (49.3 g, 0.50 mol) in water (250 ml) at 50 deg. A solution of ammonium persulfate (93 g, 0.40 mol) in water (200 ml) was then added over 30 minutes at 60 deg. The resulting mixture was then stirred at 80 deg for 40 minutes and then cooled to room temperature. The mixture was adjusted to pH8 with 25% aqueous ammonium hydroxide and extracted with diethyl ether (3×250 ml). The combined ether extracts were washed with water (200 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography (5% ethyl acetate/hexane) to give 3,6-dichloro-4-n-butylpyridazine as a pale yellow oil (14.4 g, 47%). 1H-NMR (CDCl3) 7.30 (1H, s, 5-H), 2.65 (2H, t, Bu), 1.58 (2H, m, Bu), 1.37 (2H, m, Bu), 0.91 (3H, t, Bu).

Workup

  1. extractionextracted with diethyl ether (3×250 ml)
  2. washThe combined ether extracts were washed with water (200 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-906d9684327b4214a1cc469ffdb81d84
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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