Hexane → HCID 18438078, compound

HRID 457362Notes

Reaction equation

HRID 457362 reaction equation
[CH2:1]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][NH:8][C:7](=O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].CCCCCC.CCOC(C)=O.O=P(Cl)(Cl)[Cl:32]>>[CH2:1]([C:5]1[CH:6]=[C:7]([Cl:32])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 18438121HCID 18438121, compound

Product 1

HCID 18438078HCID 18438078, compound

Conditions

Temperature
85 °C

Procedure

5-butyl-6-phenyl-2H-pyridazin-3-one (3.6 g, 15.8 mmol)) is dissolved in POCl3 (40 mL) and the solution is heated at 85° C. for 3 hours. The excess POCl3 is evaporated in vacuo and the residue is partitioned between saturated aqueous NaHCO3 solution (50 mL) and EtOAc (50 mL). The organic layer is washed with water (35 mL), brine (35 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides a yellow oil. Flash column chromatograph (silica gel, 4:1 hexane, EtOAc) provides a light yellow oil. LC-MS (M+1) 247. 1H NMR (δ, CDCl3) 7.47 (s, 5H), 7.42 (s, 1H), 2.62 (t, J=7.2 Hz, 2H), 1.43–1.53(m, 2H), 1.18–1.31 (m, 2H), 0.81 (t, J=7.5 Hz, 3H).

Workup

  1. customThe excess POCl3 is evaporated in vacuo
  2. customthe residue is partitioned between saturated aqueous NaHCO3 solution (50 mL) and EtOAc (50 mL)
  3. washThe organic layer is washed with water (35 mL), brine (35 mL)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent in vacuo
  6. customprovides a yellow oil

Sources & evidence

ORD record
ord-25a10fa896614a9bb0a1f8241b6f5827
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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