Pyridine → HCID 21185388, compound

HRID 850038Notes

Reaction equation

[CH3:1][N:2]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[NH2:3].N1C=CC=CC=1.C(#N)C.[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26]([NH:3][N:2]([CH3:1])[S:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:5])=[O:6])=[O:27]

Participants

Conditions

Temperature: 10 °C

Procedure

Into a 100 mL three necked round bottom flask equipped with a magnetic stirrer and condenser, under an atmosphere of nitrogen, was added 2-methyl-2-[(4-chlorophenyl)sulfonyl] hydrazine (5.4 g, 24.5 mmol), pyridine (1.93 g, 1.98 mL, 24.5 mmol), 4-dimethylaminopyridine (0.15 g, 1.2 mmol), and acetonitrile (50 mL). The mixture was cooled to 10° C. and 2-fluoro-6-chlorobenzoyl chloride (4.65 g, 23.4 mmol) was added dropwise at a rate such that the temperature did not rise above 10° C. The mixture was allowed to stir at RT overnight. The solvent was removed from the reaction mixture in vacuo to give an off white solid and the solid was diluted with methylene chloride and extracted with 1N HCl (20 mL), saturated sodium bicarbonate (20 mL), dried (Na2SO4), and the solvent removed in vacuo to give 1-(2-fluoro-6-chlorobenzoyl)-2-methyl-2-[(4-chlorophenyl)sulfonyl] hydrazine as a yellow oil which was used without purification.

Workup

customdid not rise above 10° C
customThe solvent was removed from the reaction mixture in vacuo
customto give an off white solid
extractionextracted with 1N HCl (20 mL), saturated sodium bicarbonate (20 mL)
dry with materialdried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-2be1e1cb13bc4b92bf614d4eb81f2a37
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015826

Reaction notes

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