Pyridine → 4-Methyl-N-(oxo-lambda~4~-sulfanylidene)benzamide

HRID 1396072Notes

Reaction equation

HRID 1396072 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7]([NH2:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[S:17](Cl)(Cl)=[O:18]>CCOCC>[S:17](=[N:9][C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)=[O:8])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 692744-Methylbenzamide

Product 1

HCID 133013154-Methyl-N-(oxo-lambda~4~-sulfanylidene)benzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

10 g of p-toluamide were suspended in 100 ml of ether and 12.5 ml of pyridine under argon. The 5.8 ml of thionyl chloride dissolved in 10 ml of ether were added dropwise at 5° C. and the mixture was stirred for a further 5 minutes. Subsequently, the cooling was removed and the mixture was stirred at room temperature for a further 16 hours. Under argon, the solid pyridinium hydrochloride was then filtered off, and then the solution was concentrated. The residue was used without further workup.

Workup

  1. additionwere added dropwise at 5° C.
  2. customSubsequently, the cooling was removed
  3. stirringthe mixture was stirred at room temperature for a further 16 hours
  4. filtrationUnder argon, the solid pyridinium hydrochloride was then filtered off
  5. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-57ba6ca22e26401894c70e6b4a637b3b
Source dataset
uspto-grants-2014_12
Patent number
US08901114B2

Reaction notes

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