Methanol → HCID 20373697, compound

HRID 1834512Notes

Reaction equation

HRID 1834512 reaction equation
CO.[Na].[SH:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.Cl[C:12]1[C:13]([C:22]#[N:23])=[N:14][C:15]([C:20]#[N:21])=[C:16](Cl)[C:17]=1Cl>CC(C)=O>[N:8]1[CH:9]=[CH:10][C:5]([S:4][C:12]2[C:13]([C:22]#[N:23])=[N:14][C:15]([C:20]#[N:21])=[C:16]([S:4][C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)[C:17]=2[S:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5360545Sodium2×HCID 122053163,4,5-Trichloropyridine-2,6-dicarbonitrileHCID 178418431pyridine-4-thiol

Product 1

HCID 20373697HCID 20373697, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 500 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a calcium chloride drying tube were placed 250 ml of methanol and 2.30 g (0.10 mol) of sodium metal. After all of the sodium had reacted, 11.11 g (0.10 mol) of 4-mercaptopyridine was added and the solution was allowed to stir for five minutes. To the resulting thiolate solution, 7.65 g (0.033 mol) of 3,4,5-trichloro-2,6-pyridinedicarbonitrile was added. The reaction mixture immediately became cloudy and orange in color. The reaction mixture was heated to reflux and then cooled. The methanol was removed in vacuo leaving a red-orange gum. Mixing of the gum with acetone, filtering off the solid and drying the latter afforded 6.89 g of the title compound as a yellow to orange powder, m.p. 186°-189° C (dec.). A 1.00 g sample was recrystallized from absolute ethanol to give a 0.25 g analytical sample as small, yellow-orange crystals, m.p. 186°-189° C (dec.). Anal. % Calcd. for C22H12N6S3 : C, 57.87; H, 2.65; N, 18.41. Found: C, 57.64; H, 2.59; N, 18.22.

Workup

  1. customIn a 500 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser
  2. customfitted with a calcium chloride drying tube
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperaturecooled
  6. customThe methanol was removed in vacuo
  7. customleaving a red-orange gum
  8. filtrationfiltering off the solid
  9. customdrying the

Sources & evidence

ORD record
ord-6c07fdb0b37341ce9527f3cc87534844
Source dataset
uspto-grants-1978_01
Patent number
US04070471

Reaction notes

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