Hydrogen Sulfide → 2-Phenyl-2-(6-methyl-3-pyridazinyl)thioacetamide

HRID 1733548Notes

Reaction equation

HRID 1733548 reaction equation
[C:1]1([CH:7]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[SH2:23]>N1C=CC=CC=1>[C:1]1([CH:7]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:8]([NH2:9])=[S:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 11127164HCID 11127164, compound

Product 1

HCID 64105372-Phenyl-2-(6-methyl-3-pyridazinyl)thioacetamideYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 1.0 g quantity (0.005 mols) of 2-phenyl-2-(3-pyridazinyl)acetonitrile was dissolved in 50 ml of dry pyridine in a sealed tube, and 4 ml of triethylamine was added. After allowing the resulting solution to stand for 1.5 hours, dry hydrogen sulfide was passed through the solution in a steady stream at room temperature for 15 minutes. The sealed mixture was then left to stand at room temperature for 24 hours. The reaction mixture was concentrated in a vacuum to give a yellow solid cake. Recrystallization of the concentrate from ethanol afforded 1.1 g (94% yield) of 2-phenyl-2-(3-pyridazinyl)thioacetamide in the form of pale yellow plates, m.p. 161° to 163° C.

Workup

  1. waitThe sealed mixture was then left
  2. waitto stand at room temperature for 24 hours
  3. concentrationThe reaction mixture was concentrated in a vacuum
  4. customto give a yellow solid cake
  5. customRecrystallization of the
  6. concentrationconcentrate from ethanol

Sources & evidence

ORD record
ord-366399ea252c4a87a051544f4afc941a
Source dataset
uspto-grants-1980_12
Patent number
US04242512

Reaction notes

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