Water → (NE)-N-[1-(6-chloropyridazin-3-yl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 2038761Notes

Reaction equation

HRID 2038761 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]([S:15]([NH2:17])=[O:16])([CH3:14])[CH3:13].O>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5](/[C:8](=[N:17]/[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])/[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 468356481-(6-Chloropyridazin-3-yl)ethan-1-one

Product 1

HCID 88959216(NE)-N-[1-(6-chloropyridazin-3-yl)ethylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(6-chloro-pyridazin-3-yl)-ethanone (34 mg, 0.22 mmol) in dry THF (1.0 mL) was added 2-methyl-propane-2-sulfinic acid amide (29 mg, 0.24 mmol). Ti(OEt)4 (0.090 mL, 0.43 mmol) was added in one portion and the reaction was heated to 60° C. for 1 h. Water was added to the reaction mixture and the resulting slurry was filtered through a pad of diatomaceous earth. The filtrate was dried over Na2SO4 and was concentrated to provide 2-methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-eth-(E)-ylidene]-amide as a crude residue that was used without purification, m/z 260.5 [M+H]+.

Workup

  1. filtrationthe resulting slurry was filtered through a pad of diatomaceous earth
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-884b4931d1f44e1da9000a7cd50a84eb
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

Loading…