Diethyl Ether → 3-(4-Chloro-1,2,5-thiadiazol-3-yl)-4-methylpyridine

HRID 1599390Notes

Reaction equation

HRID 1599390 reaction equation
[Cl:1][C:2]1[C:6]([C:7]2[CH:12]([CH3:13])[CH:11]=[CH:10][N:9](C(OC3C=CC=CC=3)=O)[CH:8]=2)=[N:5][S:4][N:3]=1.[S].CCOCC>C1C2C(CCCC2)CCC1>[Cl:1][C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[CH3:13])=[N:5][S:4][N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5362487SulfurHCID 18928232HCID 18928232, compound

Product 1

HCID 190753933-(4-Chloro-1,2,5-thiadiazol-3-yl)-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 7044DecalinSolvent

Procedure

To a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-4-methyl-1-phenoxycarbonyl-1,4-dihydropyridine (11.7 g, 35 mmol) in decalin (100 ml) was added sulfur (1.4 g, 43 mmol) and the reaction mixture was refluxed for 5 h. After cooling to room temperature, ether (100 ml) was added and the organic phases extracted with 1N HCl (2×75 ml). The aqueous phase was basified with NaOH(aq) and extracted with methylene chloride (2×100 ml). The methylene chloride phase was dried and evaporated to give solid title material in 5.47 g (74%) yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. extractionthe organic phases extracted with 1N HCl (2×75 ml)
  3. extractionextracted with methylene chloride (2×100 ml)
  4. dry with materialThe methylene chloride phase was dried
  5. customevaporated
  6. customto give solid title material in 5.47 g (74%)
  7. customyield

Sources & evidence

ORD record
ord-6881b1fa71b94bce86a5f5cb946850df
Source dataset
uspto-grants-1998_04
Patent number
US05741788

Reaction notes

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