Water → HCID 15581961, compound

HRID 1605676Notes

Reaction equation

HRID 1605676 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([NH2:10])=[S:9].O.[CH2:12](N)[C:13]#[CH:14]>C(O)C>[CH2:14]([NH:10][C:8](=[S:9])[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 239041PropargylamineHCID 30351632-Pyridineacetamide, thio-

Product 1

HCID 15581961HCID 15581961, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4.0 g. (0.026 mole) of 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 5 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 N-propargyl-2-(2-pyridyl)thioacetamide, m.p. 62°-63°C.

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-d6815c441f864c4b957d2033197b9f1f
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

Loading…