Hexane → HCID 18438078, compound

HRID 1643196Notes

Reaction equation

HRID 1643196 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-a0955b872dd840f59e8f2589b3735c98
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

Loading…