1-Hexanol → 3-(4-(Hexyloxy)-1,2,5-thiadiazol-3-yl)pyridine

HRID 1077725Notes

Reaction equation

HRID 1077725 reaction equation
[Na].Cl[C:3]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:6][S:5][N:4]=1.[CH2:14]([OH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:14]([O:20][C:3]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:6][S:5][N:4]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 81031-HexanolHCID 5360545SodiumHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole

Product 1

HCID 151801353-(4-(Hexyloxy)-1,2,5-thiadiazol-3-yl)pyridine

Conditions

Temperature
50 °C

Procedure

To a solution of sodium (230 mg, 10 mmol) in 1-hexanol (15 ml) was added 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (490 mg, 2.5 mmol). The mixture was stirred at 50° C. for 2 h and evaporated. The residue was dissolved in water and extracted with ether. The combined organic phases were dried and evaporated to give the wanted compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ether
  4. customThe combined organic phases were dried
  5. customevaporated
  6. customto give the wanted compound

Sources & evidence

ORD record
ord-0c8ba064d6de4e67902348fec5ed2312
Source dataset
uspto-grants-1996_08
Patent number
US05545638

Reaction notes

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