Sulfuric Acid → HCID 18438079, compound

HRID 1643197Notes

Reaction equation

OS(O)(=O)=O.[CH2:6]([C:10]1[CH:15]=[C:14]([Cl:16])[N:13]=[N:12][C:11]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][CH2:8][CH3:9].CCCCCC.C[CH2:30][O:31]C(C)=O>CO.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:6]([C:10]1[C:15]([CH2:30][OH:31])=[C:14]([Cl:16])[N:13]=[N:12][C:11]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 75 °C

Procedure

Concentrated H2SO4 (0.17 ml, 3.2 mmol), (NH4)2S2O8 (0.575 g, 2.52 mmol) and AgNO3 (4 mg) are added to a solution of 4-butyl-6-chloro-3-phenyl-pyridazine (0.526 g, 2.1 mmol) in MeOH (12 mL) and water (6 mL). The mixture is heated at 75° C. for 3 h and the solvent is then evaporated in vacuo. The residue is partitioned between saturated aqueous NaHCO3 solution (30 mL) and EtOAc (30 mL) and the organic layer is washed with water (25 mL), brine (25 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides a yellow oil. Flash column chromatography (silica gel, 2:1 hexane, EtOAc) provides the product as a light yellow solid. LC-MS (M+1) 277. 1H NMR (δ, CDCl3) 7.42-7.50 (m, 5H), 4.87 (s, 2H), 2.75 (t, J=8.1 Hz, 2H), 2.40 (s, 1H), 1.34-1.43 (m, 2H), 1.17-1.25 (m, 2H), 0.74 (t, J=7.5 Hz, 3H).

Workup

customthe solvent is then evaporated in vacuo
customThe residue is partitioned between saturated aqueous NaHCO3 solution (30 mL) and EtOAc (30 mL)
washthe organic layer is washed with water (25 mL), brine (25 mL)
dry with materialdried (Na2SO4)
customEvaporation of the solvent in vacuo
customprovides a yellow oil

Sources & evidence

ORD record: ord-3166e55a5da54f718409bbd2e2c81351
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119665B2

Reaction notes

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