Sodium Carbonate → 4-(1,2,3-thiadiazol-4-yl)pyridine

HRID 1762689Notes

Reaction equation

HRID 1762689 reaction equation
[C:1](=[N:9][NH:10]C(N)=O)([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].[S:14](Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[S:14]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[N:9]=[N:10]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 2755736HCID 2755736, compound

Product 1

HCID 14718104-(1,2,3-thiadiazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

16.8 g of 4-acetylpyridine semicarbazone was added to 47 ml of thionyl chloride under ice-cooling, and, after allowing to warm to room temperature, the mixture was stirred for 1 hour. 200 ml of chloroform was added to the reaction mixture, and the resulting mixture was added dropwise to an aqueous solution of sodium carbonate cooled with ice. The chloroform layer was separated, washed with water, dried and concentrated to obtain 3.4 g of 4-(1,2,3-thiadiazol-4-yl)pyridine. Melting point: 121°-123° C.

Workup

  1. temperaturecooling
  2. temperaturecooled with ice
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-19d4b9ad136843178a319c19c55eddd8
Source dataset
uspto-grants-1989_05
Patent number
US04833242

Reaction notes

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