Acetic Acid → 4-(2,6-Dichloro-4-trifluoromethylphenyl)-2-isopropylthioaniline

HRID 1823165Notes

Reaction equation

HRID 1823165 reaction equation
O.C(O)(=O)C.[CH:6]([S:9][C:10]1[CH:15]=[C:14]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[CH:13]=[CH:12][C:11]=1[N+:28]([O-])=O)([CH3:8])[CH3:7].C(SC1C=C(C2C(C(F)(F)F)=NNC=2)C=CC=1C(OC)=O)CC>C1(C)C=CC=CC=1.[Fe]>[Cl:27][C:17]1[CH:18]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:20]=[C:21]([Cl:22])[C:16]=1[C:14]1[CH:13]=[CH:12][C:11]([NH2:28])=[C:10]([S:9][CH:6]([CH3:8])[CH3:7])[CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 22170887[5-(2,6-Dichloro-4-trifluoromethylphenyl)-2-nitrophenyl]isopropyl sulfideHCID 178460720HCID 178460720, compound

Product 1

HCID 221709304-(2,6-Dichloro-4-trifluoromethylphenyl)-2-isopropylthioanilineYield 36%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent2×

Procedure

3.5 g (63.6 mmol) of iron powder, 10 m of water and 1 m of acetic acid were stirred in 20 ml toluene at 60° C. for 30 minutes, and 3.0 g (7.3 mmol) of [5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrophenyl] isopropyl sulfide (the compound prepared in Example 8 (2)) in 10 ml toluene was added dropwise. The reaction was carried out with reflux and heating for another 3 hours, and then the reaction mixture was cooled to room temperature. The insolubles were filtered off, and the filtrate was separated with water and toluene. The toluene layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.0 g of 4-(2,6-dichloro-4-trifluoromethylphenyl)-2-isopropylthioaniline (yield 36.0%) as a pale yellow dough (nD20 1.5782).

Workup

  1. temperaturewith reflux
  2. temperatureheating for another 3 hours
  3. filtrationThe insolubles were filtered off
  4. customthe filtrate was separated with water and toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-331151ca98ed4d5ba8ad4d0d0af31918
Source dataset
uspto-grants-2006_05
Patent number
US07037930B2

Reaction notes

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