Water → HCID 71279191, compound

HRID 1621156Notes

Reaction equation

HRID 1621156 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[C:14]1([C:5]2[N:4]=[C:3]([CH2:2][C:20]#[N:21])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[N:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86677493HCID 86677493, compound

Product 1

HCID 71279191HCID 71279191, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(5-(chloromethyl)-3-phenyl-1H-1,2,4-triazol-1-yl)pyridine (130 mg, 480 μmol) and potassium cyanide (43.8 mg, 672 μmol) in DMSO (3.5 mL) was heated to 50° C. for 1.5 h. The cooled reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic phase was washed with water (2×25 mL), dried over MgSO4 and concentrated in vacuo to give 110 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as white solid (30 mg, 114 μmol, 23.7%).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic phase was washed with water (2×25 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25ef77a7f20b43aba9fbd4e8ee7abf73
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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