Sodium Methoxide → HCID 136334002, compound

HRID 1520362Notes

Reaction equation

HRID 1520362 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]=[N:15][CH:14]=1)=O)(=[O:3])[NH2:2].C[O-].[Na+]>C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][C:13]([C:11]2[NH:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:10]=2)=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67298039HCID 67298039, compound

Product 1

HCID 136334002HCID 136334002, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 100 mL round-bottom flask equipped with a Dean-Stark trap was charged with a mixture of N-(2-carbamoylphenyl)pyridazine-4-carboxamide (300 mg, 1.0 eq.), sodium methoxide (401 mg, 7.4 mmol, 6.0 eq.) and 10 mL of anhydrous toluene. The reaction mixture was heated to 110° C. and refluxed overnight. After cooling, the volatiles were removed in vacuo and the residue was quenched with a saturated aqueous solution of NH4Cl (10 mL). The pH of the mixture was adjusted to 3 with 10% HCl in water. The solution was extracted with DCM (50 ml×3). The combined organic layers were washed with brine, dried over Na2SO4. After filtration and evaporation, 88 mg of a yellow solid was obtained, LCMS m/z=225.1 (M+1) (Method A) (retention time=1.10 min) which was used in the next step without further purification.

Workup

  1. customA 100 mL round-bottom flask equipped with a Dean-Stark trap
  2. temperaturerefluxed overnight
  3. temperatureAfter cooling
  4. customthe volatiles were removed in vacuo
  5. customthe residue was quenched with a saturated aqueous solution of NH4Cl (10 mL)
  6. extractionThe solution was extracted with DCM (50 ml×3)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-c0e7a3651b1a4e61b2face27b7284b34
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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