Toluene → HCID 20317453, compound

HRID 867082Notes

Reaction equation

HRID 867082 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14](O)[CH2:15][N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O.C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:24][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 20490886HCID 20490886, compound

Product 1

HCID 20317453HCID 20317453, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

150 g (0.5 mole) of 1-(2-[4"-chloro-4'-biphenylyl]-2-hydroxy-ethyl)-1,2,4-triazole were dissolved in 2 liters of chloroform and heated to the boil, while stirring. 90g (0.75 mole) of thionyl chloride were slowly added dropwise thereto. The reaction mixture was heated for 12 hours under reflux and after cooling, 1.5 liters of toluene were added. The hydrochloride of 1-(2-chloro-2-[4'(4"-chlorophenyl)-phenyl]-ethyl)-1,2,4-triazole, which thereupon precipitated, was filtered off and taken up in 2 liters of water. The free base was obtained by adding sodium bicarbonate, and was taken up in chloroform. After drying over sodium sulfate, the solvent was distilled off and the residue soldified to crystals. 148 g (92% of theory) of 1-(2-chloro-2-[4"-chloro-4'-biphenylyl]ethyl)-1,2,4-triazole of melting point 118° C. were obtained.

Workup

  1. temperatureheated to the boil
  2. temperatureThe reaction mixture was heated for 12 hours
  3. temperatureunder reflux
  4. temperatureafter cooling
  5. customThe hydrochloride of 1-(2-chloro-2-[4'(4"-chlorophenyl)-phenyl]-ethyl)-1,2,4-triazole, which thereupon precipitated
  6. filtrationwas filtered off
  7. customThe free base was obtained
  8. dry with materialAfter drying over sodium sulfate
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-7e46f44b38b942eba9fb5dc202712aa9
Source dataset
uspto-grants-1978_07
Patent number
US04102891

Reaction notes

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