Pyridine → 2-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide

HRID 1076374Notes

Reaction equation

HRID 1076374 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH3:15][O:16][CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:18]([N:20]([CH3:22])[CH3:21])=O.N1C=CC=CC=1.[OH-].[Na+]>O>[CH3:15][O:16][CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:18]([N:20]([CH3:22])[CH3:21])=[S:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 21486904HCID 21486904, compound

Product 1

HCID 155819592-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus pentasulfide (4 g.) is added to 9.7 g. of 2-methoxy-N,N-dimethyl-2-(2-pyridyl)acetamide in 25 ml. of pyridine. The mixture is heated on a steam bath for 2 hours, then 250 ml. of water and 10 ml. of 5% aqueous sodium hydroxide solution are added. The mixture is extracted with chloroform and the extracts are dried and concentrated and the residue is recrystallized to give 2-methoxy-N,N-dimethyl-2-(2-pyridyl)-thioacetamide.

Workup

  1. temperatureThe mixture is heated on a steam bath for 2 hours
  2. extractionThe mixture is extracted with chloroform
  3. customthe extracts are dried
  4. concentrationconcentrated
  5. customthe residue is recrystallized

Sources & evidence

ORD record
ord-4edc2293f27442a7ad821920b91a2c8e
Source dataset
uspto-grants-1976_05
Patent number
US03956494

Reaction notes

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