6-Methyl-2-pyridinecarboxaldehyde → (NE)-2-methyl-N-[(6-methyl-2-pyridinyl)methylidene]propane-2-sulfinamide

HRID 1255855Notes

Reaction equation

HRID 1255855 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH3:8][C:9]1[N:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]([S:5](/[N:7]=[CH:15]/[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:8])[N:14]=1)=[O:6])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 87570993(NE)-2-methyl-N-[(6-methyl-2-pyridinyl)methylidene]propane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylpropane-2-sulfinamide (0.18 g, 1.49 mmol) in methylene chloride (3 mL) was added copper sulfate (0.24 g, 1.49 mmol) followed by 6-methylpyridine-2-carbaldehyde (0.2 g, 1.63 mmol). The reaction was stirred at ambient temperature for 16 hours, then filtered through a pad of celite (washing with methylene chloride) and evaporated in vacuo to give crude 2-methyl-N-[(1E)-(6-methylpyridin-2-yl)methylene]propane-2-sulfinamide. LC-MS EIMS: m/z 225.1 [M+H]+.

Workup

  1. filtrationfiltered through a pad of celite (washing with methylene chloride)
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-aeca80bdc9704b6ca530fe5e3360931c
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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