1-Hexanol → 3-(3-Hexyloxy-1,2,5-thiadiazol-4-yl)-6-methylpyridine

HRID 1600322Notes

Reaction equation

HRID 1600322 reaction equation
[H-].[Na+].[CH2:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:11]1[C:15]([C:16]2[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[N:14][S:13][N:12]=1>C1COCC1>[CH2:3]([O:9][C:11]1[C:15]([C:16]2[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[N:14][S:13][N:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 190752683-(3-Chloro-1,2,5-thiadiazol-4-yl)-6-methylpyridine

Product 1

HCID 190755123-(3-Hexyloxy-1,2,5-thiadiazol-4-yl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.72 g, 15 mmol) was dissolved in dry THF (20 ml) and 1-hexanol (1.53 g, 15 mmol) and a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-6-methylpyridine (1.06 g, 5 mmol) in dry THF (15 ml) was added. The reaction mixture was stirred for 2 h. Afteraddition of water the mixture was extracted with ether, and the ether phasewas dried and evaporated. The residue consisted of the crude title compound, which was used without further purification.

Workup

  1. extractionAfteraddition of water the mixture was extracted with ether
  2. dry with materialthe ether phasewas dried
  3. customevaporated
  4. customwas used without further purification

Sources & evidence

ORD record
ord-d4c417f90a8e4199b9e81f94640c9094
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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