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

HRID 72343

Reaction equation

HRID 72343 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

p-Toluamide (76 g) and pyridine (95.5 ml) were initially charged in dry ether (600 ml) and, while cooling with ice, thionyl chloride (70.2 g) in ether (200 ml) was added dropwise. The mixture was stirred at room temperature overnight. With exclusion of moisture, the pyridine hydrochloride was then filtered off and washed with ether (100 ml). The solution was concentrated under reduced pressure and the residue (83.5 g) was used without further purification.

Workup

  1. additionwas added dropwise
  2. filtrationWith exclusion of moisture, the pyridine hydrochloride was then filtered off
  3. washwashed with ether (100 ml)
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe residue (83.5 g) was used without further purification

Sources & evidence

ORD record
ord-40888b505acd4683b7f2770905b7cad1
Source dataset
uspto-grants-2014_09
Patent number
US08828995B2

Linked notes

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