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

HRID 744601Notes

Reaction equation

HRID 744601 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-79a787310c6942bf92ed18903514d40a
Source dataset
uspto-grants-1996_09
Patent number
US05559138

Reaction notes

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