Formaldehyde → 1-(4-Chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-one

HRID 637864Notes

Reaction equation

HRID 637864 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([C:13]([CH2:15][N:16]1[N:20]=[CH:19][N:18]=[CH:17]1)=[O:14])([CH3:12])[CH3:11].C=O.N1CCCC[CH2:24]1>C1(C)C=CC=CC=1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:24][CH:15]([N:16]2[CH:17]=[N:18][CH:19]=[N:20]2)[C:13](=[O:14])[C:10]([CH3:9])([CH3:11])[CH3:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 7815p-ChlorothiophenolHCID 8082PiperidineHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Product 1

HCID 131913651-(4-Chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-oneYield 28%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 72.5 g (0.5 mol) of 4-chlorothiophenol, 100.2 g (0.6 mol) of 1,2,4-triazol-1-yl-pinacolin, 18 g (0.6 mol) of paraformaldehyde, 15 g of acetic acid and 5 ml of piperidine in 600 ml of toluene was heated under reflux in a water separator. After the water had been separated off, the reaction solution was washed with water, dried over sodium sulphate, filtered, and concentrated in vacuo. The oily residue was chromatographed over a silica gel column (mobile phase: chloroform). 45 g (28% of theory) of 1-(4-chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-one of melting point 67° C. were obtained.

Workup

  1. temperaturewas heated
  2. customAfter the water had been separated off
  3. washthe reaction solution was washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was chromatographed over a silica gel column (mobile phase: chloroform)

Sources & evidence

ORD record
ord-55fcba6076a7427b8be23bfa701bd6d6
Source dataset
uspto-grants-1985_12
Patent number
US04559077

Reaction notes

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