Water → HCID 21540450, compound

HRID 1076379Notes

Reaction equation

HRID 1076379 reaction equation
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH2:6])=[S:5].O.[CH2:14](N)[C:15]#[CH:16]>C(O)C>[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([NH:6][CH2:16][C:15]#[CH:14])=[S:5]

Participants

5

Reactant 3

HCID 962WaterHCID 239041PropargylamineHCID 15581956HCID 15581956, compound

Product 1

HCID 21540450HCID 21540450, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4.4 g. (0.026 mole) of 2-methoxy-2-(2-pyridyl)thioacetamide in 20 ml. of water at 0°C. is added 2.9 g. (0.053 mole) of propargylamine with stirring and the resulting suspension is allowed to stand overnight at 5°C. Ethanol (5 ml.) is added and the mixture is stirred for five hours, then extracted with dichloromethane. The extracts are dried and concentrated. The residue is chromatographed on a silica gel "dry-column," using 1:10 ethyl acetate/ether as the eluant. The product fraction is treated with charcoal, filtered, concentrated and the residue is recrystallized from benzene/ligroin to give 2-methoxy-N-propargyl-2-(2-pyridyl)thioacetamide.

Workup

  1. extractionextracted with dichloromethane
  2. customThe extracts are dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on a silica gel "dry-column,"
  5. additionThe product fraction is treated with charcoal
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue is recrystallized from benzene/ligroin

Sources & evidence

ORD record
ord-6f36676f5a5744a7b54cd3de0b431dc6
Source dataset
uspto-grants-1976_05
Patent number
US03956494

Reaction notes

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