Dichloromethane → HCID 59242656, compound

HRID 1630461Notes

Reaction equation

HRID 1630461 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[N:12][NH:11][C:10](=O)[CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.C(=O)([O-])O.[Na+].ClCCl>C(#N)C>[Cl:21][C:10]1[N:11]=[N:12][C:13]([C:14]([F:17])([F:16])[F:15])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate2×HCID 59242648HCID 59242648, compound

Product 1

HCID 59242656HCID 59242656, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

To a stirred solution of 5-(4-fluorophenyl)-6-trifluoromethyl-2H-pyridazine-3-one (D6) (0.96 g, 3.7 mmol) in acetonitrile (10 ml) was added phosphorous oxychloride (0.866 ml, 9.3 mmol) and the reaction was stirred at 180° C. for 30 min., under microwave irradiation. After this period, the reaction mixture was poured into a saturated solution of sodium hydrogen carbonate, ice and dichloromethane. Further solid sodium hydrogen carbonate was then added until gas evolution had ceased. The organic layer was then separated, dried (Na2SO4) and the solvents evaporated in vacuo to yield D7 (0.81 g, 79%). Only traces of the undesired isomer were detected after work-up. C11H5ClF4N2 requires 276; Found 277 (MH+).

Workup

  1. waitAfter this period
  2. customThe organic layer was then separated
  3. dry with materialdried (Na2SO4)
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-0c445340478b49eaaa00860ea98431cf
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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