Thionyl Chloride → HCID 59436266, compound

HRID 2089750Notes

Reaction equation

HRID 2089750 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=[C:3]1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1.S(Cl)(Cl)=O>C(Cl)Cl>[N:27]1([C:18](=[N:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]2[C:2](=[O:1])[CH:7]=[CH:6][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=3)[N:4]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1481283HCID 1481283, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 59436266HCID 59436266, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-oxo-N-phenyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (0.153 g, 0.426 mmol), 1H-benzo[d][1,2,3]triazole (0.201 g, 1.69 mmol) and thionyl chloride (0.06 mL, 0.82 mmol) in methylene chloride (2 mL) was heated under microwave heating conditions at 80 watts of power for 10 min. After that time, the reaction was concentrated and the crude product purified by flash column chromatography (silica gel, hexanes to ethyl acetate) to give 0.114 g (58%) of 3-[1H-benzotriazol-1-yl(phenylimino)methyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as a pale red solid that was used without further characterization.

Workup

  1. temperatureheating conditions at 80 watts of power for 10 min
  2. concentrationAfter that time, the reaction was concentrated
  3. customthe crude product purified by flash column chromatography (silica gel, hexanes to ethyl acetate)

Sources & evidence

ORD record
ord-bf8cce1a5abc47d5b85f147215aba950
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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