Methanol → HCID 23094117, compound

HRID 2249407Notes

Reaction equation

HRID 2249407 reaction equation
[C:1]([C:4]1[C:5](=[O:19])[NH:6][N:7]=[C:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)[CH:9]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:24]O>>[O:17]1[C:13]2[CH:12]=[CH:11][C:10]([C:8]3[CH:9]=[C:4]([C:1]([O:3][CH3:24])=[O:2])[C:5](=[O:19])[NH:6][N:7]=3)=[CH:18][C:14]=2[CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 230941044-Carboxy-6-(2,3-dihydro-1-benzofuran-5-yl)-2H-pyridazin-3-one

Product 1

HCID 23094117HCID 23094117, compound

Conditions

Temperature
80 °C

Procedure

4-Carboxy-6-(2,3-dihydro-1-benzofuran-5-yl)-2H-pyridazin-3-one (5.9 g, 22.8 mmol) was suspended in methanol (100 mL), and thionyl chloride (3 g, 25.1 mmol) was added dropwise to the suspension under cooling with ice, followed by stirring for three hours at 80° C. The temperature of the reaction mixture was reduced to room temperature, and the solvent was removed under reduced pressure. Water was added to the residue under cooling on ice, and the formed precipitates were collected through filtration and washed with water, followed by drying, to thereby yield 4.90 g of the title compound as pale yellow micro-needles (78.8%).

Workup

  1. temperatureunder cooling with ice
  2. customwas reduced to room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionWater was added to the residue
  5. temperatureunder cooling on ice
  6. customthe formed precipitates
  7. filtrationwere collected through filtration
  8. washwashed with water
  9. customby drying

Sources & evidence

ORD record
ord-7ab44c3252c04b3fb592bc15ab239603
Source dataset
uspto-grants-2008_01
Patent number
US07314877B2

Reaction notes

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