Water → HCID 178460817, compound

HRID 868933Notes

Reaction equation

HRID 868933 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10](=[S:12])[NH:9][N:8]=2)=[CH:3][CH:2]=1.Br[CH2:14][C:15]#[CH:16].C([O-])(=O)C.[Na+].O>CN(C=O)C>[CH2:16]([S:12][C:10]1[NH:11][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[N:8][N:9]=1)[C:15]#[CH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 517045Sodium AcetateHCID 178527915HCID 178527915, compound

Product 1

HCID 178460817HCID 178460817, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione (2 g, 11.2 mmol), 3-bromoprop-1-yne (1.47 g, 12.3 mmol) and sodium acetate (5.34 g, 65.1 mmol) in DMF (20 mL) was stirred for 6 h at room temperature. The reaction mixture was then poured into water (50 mL) and extracted with DCM. The combined organic layers were washed with water three times, dried with Na2SO4, filtered and concentrated to obtain the title compound (1.5 g).

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with water three times
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12e9c05b8d6b4ee080df7d05e172a6f5
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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