Water → 3-(3-(3-Pentynyloxy)-1,2,5-thiadiazol-4-yl)pyridine

HRID 744622Notes

Reaction equation

HRID 744622 reaction equation
[CH2:1]([OH:6])[CH2:2][C:3]#[C:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:11]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][S:13][N:14]=1.O>O1CCCC1>[CH2:1]([O:6][C:10]1[C:11]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][S:13][N:14]=1)[CH2:2][C:3]#[C:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 662953-Pentyn-1-olHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole

Product 1

HCID 190752603-(3-(3-Pentynyloxy)-1,2,5-thiadiazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-pentyn-1-ol (750 mg, 9 mmol) and sodium hydride (310 mg, 9 mmol) in dry tetrahydrofuran was added a solution of 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (590 mg, 3 mmol) in dry tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ether. The ether phase was dried and evaporated to give the title compound.

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe ether phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-caefcf6a71b3468cadb718848dfcc581
Source dataset
uspto-grants-1996_09
Patent number
US05559138

Reaction notes

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