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

HRID 865166
Notes
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Reaction equation

HRID 865166 reaction equation
[CH2:1]([OH:7])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6].[H-].[Na+].Cl[C:11]1[C:15]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:14][S:13][N:12]=1.O>O1CCCC1>[CH2:1]([O:7][C:11]1[C:15]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:14][S:13][N:12]=1)[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 52811673-HexenolHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole

Product 1

HCID 70144893cis-3-(3-(3-Hexenyloxy)-1,2,5-thiadiazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

To a solution of cis-3-hexen-1-ol (900 mg, 9 mmol) and sodium hydride (310 mg, 9 mmol) in dry tetrahydrofuran was added a solution of 3-(3-chloro-1,2,5-thiadiazol-4-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-d361da8fa92f41dca0e00e0f38ae369a
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05565475

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes