Dimethylthiocarbamoyl chloride → 2-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide

HRID 1414259Notes

Reaction equation

HRID 1414259 reaction equation
C1([Li])C=CC=CC=1.C1C=CC=CC=1.CCOCC.[CH3:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[S:31]>O.C1C=CC=CC=1>[CH3:19][O:20][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:30]([N:29]([CH3:33])[CH3:28])=[S:31]

Participants

7

Reactant 4

HCID 27871Dimethylthiocarbamoyl chlorideHCID 2532202-(Methoxymethyl)pyridineHCID 22174802Benzene etherHCID 178506676HCID 178506676, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

To 0.10 mole of phenyl lithium in 100 ml. of benzene/ether at 0° C. is added dropwise 10.6 g. (0.084 mole) of 2-(methoxymethyl)pyridine dissolved in 75 ml. of benzene. To this mixture is added dropwise 10.0 g. (0.081 mole) of N,N-dimethylthiocarbamoyl chloride in 100 ml. of benzene. The resulting mixture is stirred at room temperature overnight, then poured into 100 ml. of water and acidified. The organic phase is extracted once with dilute aqueous acid. The combined aqueous phases are extracted twice with ether, then made basic to about pH 10 and extracted three times with chloroform. The combined chloroform extracts are dried over magnesium sulfate and the solvent is removed by evaporation. The residue is chromatographed, then distilled in vacuo to give 2-methoxy-N,N-dimethyl-2-(2-pyridyl)thioacetamide.

Workup

  1. additionTo this mixture is added dropwise 10.0 g
  2. additionpoured into 100 ml
  3. extractionThe organic phase is extracted once with dilute aqueous acid
  4. extractionThe combined aqueous phases are extracted twice with ether
  5. extractionextracted three times with chloroform
  6. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  7. customthe solvent is removed by evaporation
  8. customThe residue is chromatographed
  9. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-3061b312e1224f7f82a49ed558534e2a
Source dataset
uspto-grants-1977_01
Patent number
US04001241

Reaction notes

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