O-Xylene → 3-(1,3,4-Thiadiazol-2-yl)pyridine

HRID 329608

Reaction equation

HRID 329608 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2O[CH:9]=[N:10][N:11]=2)[CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:13].C1(C)C(C)=CC=CC=1>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:13][CH:9]=[N:10][N:11]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 40231652-(Pyridin-3-yl)-1,3,4-oxadiazole

Product 1

HCID 198712843-(1,3,4-Thiadiazol-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.5 g of the above prepared 2-(3-pyridyl)-1,3,4-oxadiazole, 8.5 g of phosphorus pentasulfide and 70 ml of xylene is stirred for 16 hours at 150°-160° C. To the cooled reaction mixture are added 50 ml of water and stirring is continued for another 5 minutes. The reaction mixture is then filtered. The filter residue is taken up in 100 ml of 10% sodium hydroxide solution. After extraction with chloroform, the organic phase is washed with water, dried and concentrated. After purification by column chromatography over silica gel with a 95:5 mixture of chloroform/ethanol as eluant, the crude 2-(3-pyridyl)-1,3,4-thiadiazole (compound 1) of the formula ##STR8## with a melting point of 64°-67° C., is obtained.

Workup

  1. additionA mixture of 5.5 g of the
  2. customTo the cooled reaction mixture
  3. stirringstirring
  4. waitis continued for another 5 minutes
  5. filtrationThe reaction mixture is then filtered
  6. extractionAfter extraction with chloroform
  7. washthe organic phase is washed with water
  8. customdried
  9. concentrationconcentrated
  10. customAfter purification by column chromatography over silica gel
  11. additionwith a 95:5 mixture of chloroform/ethanol as eluant

Sources & evidence

ORD record
ord-a2c580c2c4c74133a7367a1650251ce9
Source dataset
uspto-grants-1990_01
Patent number
US04892880

Linked notes

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