Chloroform → 3-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(4-trifluoromethoxyphenyl)phenyl]-1-methyl-1H-1,2,4-triazole

HRID 52217Notes

Reaction equation

HRID 52217 reaction equation
[CH3:1][N:2](S(C)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].[F:18][C:19]([F:36])([F:35])[O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:34]=C[C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.ClC1C=CC=CC=1.[CH:44]([Cl:47])(Cl)Cl>[Fe](Cl)(Cl)Cl>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=1[C:4]1[N:32]=[C:31]([C:30]2[CH:29]=[CH:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:35])[F:36])=[CH:26][CH:25]=3)=[CH:34][C:44]=2[Cl:47])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7964ChlorobenzeneHCID 214636134-[4-(Trifluoromethoxy)phenyl]benzonitrileHCID 53690004N-methyl-N-(methanesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

Product 1

HCID 214635953-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(4-trifluoromethoxyphenyl)phenyl]-1-methyl-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(methanesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.50 g), 4-(4-trifluoromethoxyphenyl)benzonitrile (1.56 g), anhydrous iron (III) chloride (0.90 g) and chlorobenzene (20 ml) is stirred at an oil bath temperature of 140° C. for 1 hour. After cooling, the reaction mixture is dissolved in chloroform (300 ml), washed with dilute hydrochrolic acid, dilute aqueous solution of sodium hydroxide and saline in this order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexane-ethyl acetate as eluent to give 1.80 g of desired compound (refractive index: 1.5925).

Workup

  1. temperatureAfter cooling
  2. washwashed
  3. additionwith dilute hydrochrolic acid, dilute aqueous solution of sodium hydroxide and saline in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate is purified by silica gel column chromatography
  7. additionusing mixed solvent of hexane-ethyl acetate as eluent

Sources & evidence

ORD record
ord-4692f2c9569945718b88618a5fdb2077
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Reaction notes

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