Acetone → HCID 20558637, compound

HRID 1659859Notes

Reaction equation

HRID 1659859 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([SH:10])=[N:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([CH3:20])=O>>[CH2:20]([S:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)[C:18]#[CH:17]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 178526723C5H4N2O2S

Product 1

HCID 20558637HCID 20558637, compound

Procedure

7 g of 5-nitro-pyridine-2-thiol are suspended in acetone, and 5 g of potassium carbonate are added. There are then added 6 g of 3-bromopropine-1, and, after the exothermic reaction has finished, the reaction mixture is refluxed for about 30 minutes. The solution obtained is poured onto ice, and the precipitate occurring is filtered off. The crude product is purified by recrystallisation from methanol to yield 2-propargylthio-5-nitropyridine, m.p. 98°-99.5° C.

Workup

  1. customafter the exothermic reaction
  2. temperaturethe reaction mixture is refluxed for about 30 minutes
  3. customThe solution obtained
  4. additionis poured onto ice
  5. filtrationthe precipitate occurring is filtered off
  6. customThe crude product is purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-045bf79a11f94178aa183aa8bdb6877b
Source dataset
uspto-grants-1981_12
Patent number
US04305946

Reaction notes

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