Triethylamine → 6-Trifluoromethoxy-1-trifluoromethylsulphenylindazole

HRID 868175Notes

Reaction equation

HRID 868175 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[F:22][C:23]([F:27])([F:26])[S:24]Cl>C1(C)C=CC=CC=1>[F:14][C:2]([F:1])([F:13])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[S:24][C:23]([F:27])([F:26])[F:22])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67900Methanesulfenyl chloride, trifluoro-HCID 137129976-(Trifluoromethoxy)-1H-indazole

Product 1

HCID 137130126-Trifluoromethoxy-1-trifluoromethylsulphenylindazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.2 g (0.1 mole) of 6-trifluoromethoxyindazole and 10.1 g (0.1 mole) of triethylamine in 125 ml of toluene are heated to 80° to 85° C., and 13.6 g (0.1 mole) of trifluoromethanesulphenyl chloride are then passed in the course of one hour and the mixture is stirred for a further hour at this temperature. After cooling, the precipitated triethylamine hydrochloride is filtered off with suction and rinsed with toluene. The filtrate, combined with the wash liquor, is washed twice with water. After drying (MgSO4) the volatile constituents are removed by distillation under a water pump vacuum. The oily crude product is purified by distillation under an oil pump vacuum. Boiling point 62°/0.05 mbar. Yield: 16.2 g (46% of theory).

Workup

  1. customare then passed in the course of one hour
  2. temperatureAfter cooling
  3. filtrationthe precipitated triethylamine hydrochloride is filtered off with suction
  4. washrinsed with toluene
  5. washis washed twice with water
  6. dry with materialAfter drying (MgSO4) the volatile constituents
  7. customare removed by distillation under a water pump vacuum
  8. distillationThe oily crude product is purified by distillation under an oil pump vacuum

Sources & evidence

ORD record
ord-ffd70e6dcf6542288e1094786099fbe2
Source dataset
uspto-grants-1988_10
Patent number
US04778511

Reaction notes

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