Acetone → HCID 13088592, compound

HRID 2164701Notes

Reaction equation

HRID 2164701 reaction equation
B([O-])=O.[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([S:25][CH3:26])[CH:13]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][CH:7]=1.[Cl-].[Ca+2].[Cl-].CC(C)=O>O.C(O)(C)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([S:25][CH3:26])[CH:13]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH:14]([OH:19])[C:15]([CH3:18])([CH3:16])[CH3:17])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 145326Sodium metaborateHCID 5284359Calcium ChlorideHCID 13088591HCID 13088591, compound

Product 1

HCID 13088592HCID 13088592, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 2.7 g (0.0703 mol) of sodium boranate in 25 ml of water was added dropwise to a suspension of 33.75 g (0.1 mol) of 1-(4-chlorophenyl)-4,4-dimethyl-1-methylthio-2-(1,2,4-triazol-1-yl)-pentan-3-one and 7.6 g (0.0683 mol) of anhydrous calcium chloride in 200 ml of isopropanol at -5° C. The mixture was then stirred for 15 hours. After having added 20 ml of acetone the mixture was evaporated down in vacuo. The residue was stirred into water and the mixture was repeatedly extracted by shaking with methylene chloride. The methylene chloride phase was dried over sodium sulphate, filtered and evaporated down in vacuo. 32.6 g (96% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-1-methylthio-2-(1,2,4-triazol-1-yl)-pentan-3-ol, of melting point 58°-60° C., were obtained.

Workup

  1. customwas evaporated down in vacuo
  2. stirringThe residue was stirred into water
  3. extractionthe mixture was repeatedly extracted
  4. stirringby shaking with methylene chloride
  5. dry with materialThe methylene chloride phase was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated down in vacuo

Sources & evidence

ORD record
ord-c037d3d5c9fa4d949b8db719de917705
Source dataset
uspto-grants-1985_03
Patent number
US04507141

Reaction notes

Loading…