Acetonitrile → HCID 13518432, compound

HRID 2352354Notes

Reaction equation

HRID 2352354 reaction equation
[C:1]1([CH2:7][C@:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([OH:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:1]1([CH2:7][C@:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([OH:21])[CH2:9][N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 14304306HCID 14304306, compound

Product 1

HCID 13518432HCID 13518432, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 87 g (0.23 mol) of (2R)-1,2-diphenyl-2-hydroxy-3-tosyloxy-propane, 70 g (1 mol) of 1,2,4-triazole, 70 g (0.5 mol) of potassium carbonate and 800 ml of acetonitrile is refluxed for 16 hours with stirring. The reaction mixture is then poured into water, and the product which precipitates out is filtered off under suction. In order to remove any undesired biproducts which are still present, the product is dissolved in chloroform and filtered through a silica gel column, a mixture of chloroform/ethyl acetate=1:1 being used as eluent. The eluate is evaporated under reduced pressure. In this fashion, 32.5 g (51% of theory) of (2R)-1,2-diphenyl-2-hydroxy-3-(1,2,4-triazol-1-yl)-propane are obtained in the form of a solid of melting point 134° C. [α]D20 =-2.7° (c=2.75/CHCl3)

Workup

  1. temperatureis refluxed for 16 hours
  2. customthe product which precipitates out
  3. filtrationis filtered off under suction
  4. customIn order to remove any undesired biproducts which
  5. dissolutionthe product is dissolved in chloroform
  6. filtrationfiltered through a silica gel column
  7. additiona mixture of chloroform/ethyl acetate=1:1
  8. customThe eluate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d5130dae99e40a58b90190c07fa2ec2
Source dataset
uspto-grants-1989_10
Patent number
US04876353

Reaction notes

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