1-Pentanol → 3-(3-Pentyloxy-1,2,5-thiadiazol-4-yl)pyridine

HRID 1728676Notes

Reaction equation

HRID 1728676 reaction equation
[Na].Cl[C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][S:6][N:7]=1.[CH2:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:14]([O:19][C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][S:6][N:7]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 62761-PentanolHCID 5360545SodiumHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole

Product 1

HCID 151801343-(3-Pentyloxy-1,2,5-thiadiazol-4-yl)pyridine

Conditions

Temperature
50 °C

Procedure

To a solution of sodium (230 mg, 10 mmol) in 1-pentanol (20 ml) was added 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (490 mg, 2.5 mmol). The mixture was stirred at 50° C. for 3 h and evaporated. The residue was dissolved in water and extracted with methylene chloride. 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 methylene chloride
  4. customThe combined organic phases were dried
  5. customevaporated
  6. customto give the wanted compound

Sources & evidence

ORD record
ord-161a19bee77f4a1da4bf6c35f552eeba
Source dataset
uspto-grants-1994_07
Patent number
US05328925

Reaction notes

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