Water → HCID 58137367, compound

HRID 1907824Notes

Reaction equation

HRID 1907824 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[CH3:9][O:10][C:11]1[N:12]=[N+:13]([O-:21])[C:14]([CH3:20])=[CH:15][C:16]=1[N+]([O-])=O.O>C(Cl)Cl>[CH3:9][O:10][C:11]1[N:12]=[N+:13]([O-:21])[C:14]([CH3:20])=[CH:15][C:16]=1[O:4][CH2:3][C:2]([F:6])([F:5])[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 64053053-methoxy-6-methyl-4-nitropyridazine 1-oxide

Product 1

HCID 58137367HCID 58137367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

2,2,2-Trifluoroethanol (3 ml) was initially charged at RT and admixed with sodium hydride (403 mg) in portions while cooling with ice. Thereafter, the reaction mixture was heated to 55° C. for 2 h and then 3-methoxy-6-methyl-4-nitropyridazine 1-oxide solution (500 mg, dissolved in 3 ml of 2,2,2-trifluoroethanol) was added dropwise. After stirring at RT for 1 h, the mixture was heated to 55° C. for 2.5 h. After standing at RT overnight, the mixture was admixed with water and DCM. After removing the DCM phase, the aqueous phase was extracted three times with DCM and the combined DCM phases were dried over sodium sulfate, filtered and concentrated. 571 mg of the title compound were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturethe mixture was heated to 55° C. for 2.5 h
  3. waitAfter standing at RT overnight
  4. customAfter removing the DCM phase
  5. extractionthe aqueous phase was extracted three times with DCM
  6. dry with materialthe combined DCM phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f4ffcac51f9143c9a94b3129ee6733c7
Source dataset
uspto-grants-2013_12
Patent number
US08598177B2

Reaction notes

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