Sulfuric Acid → HCID 21187524, compound

HRID 1383840Notes

Reaction equation

HRID 1383840 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH:14]1(C(O)=O)[CH2:18][CH2:17][CH2:16][CH2:15]1>O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][C:7]=1[CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 18840Cyclopentanecarboxylic acidHCID 673313,6-Dichloropyridazine

Product 1

HCID 21187524HCID 21187524, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3,6-Dichloropyridazine (10 g) was suspe n ded in water (200 ml), conc. H2SO4 (19.7 g) and cyclopentane carboxylic acid (32.7 g) was added and the reaction degassed under N2 at 70° C. Silver nitrate (2.28 g) was added followed by dropwise a ddition of ammonium persulfate (45.9 g) in water (120 ml). After ail additional one hour heating at 70° C., the reaction was poured onto ice, basfied to pH 8-9 with aqueous ammonium hydroxide and extracted into ethyl acetate (3×500 ml), dried (MgSO4) and evaporated to dryness. Purified with hexane-ethyl acetate mixtures to obtain pure product (13.4 g). 1H NMR (360 MHz, CDCl3) δ1.57 (2 H, m), 1.82 (4 H, m), 2.20 (1 H, m), 3.30 (1 H, m), 7.38 (1 H, s); MS (ES+) m/e 217 [MH]+.

Workup

  1. customthe reaction degassed under N2 at 70° C
  2. additionSilver nitrate (2.28 g) was added
  3. additionthe reaction was poured onto ice
  4. extractionextracted into ethyl acetate (3×500 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customPurified with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-fbba14c76d744c7e85d4a6bbc141efe5
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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