2-Propanethiol → [5-(2,6-Dichloro-4-trifluoromethylphenyl)-2-nitrophenyl]isopropyl sulfide

HRID 1823159Notes

Reaction equation

HRID 1823159 reaction equation
[H-].[Na+].[CH:3]([SH:6])([CH3:5])[CH3:4].[H][H].Cl[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-:30])=[O:29]>CN(C)C=O>[Cl:22][C:21]1[CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=[C:17]([Cl:27])[C:16]=1[C:14]1[CH:13]=[CH:12][C:11]([N+:28]([O-:30])=[O:29])=[C:10]([S:6][CH:3]([CH3:5])[CH3:4])[CH:15]=1

Participants

6

Reactant 4

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 221709381-Chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22170887[5-(2,6-Dichloro-4-trifluoromethylphenyl)-2-nitrophenyl]isopropyl sulfideYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.33 g (8.3 mmol) of 60% sodium hydride was stirred in 50 ml of N,N-dimethylformamide at room temperature while 0.7 g (9.2 mmol) of isopropyl mercaptan was added dropwise. After generation of hydrogen was over, 3.0 g (8.1 mmol) of 1-chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene was added, and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into about 200 ml of ice-cold water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate was washed with 100 ml of water twice and dried out anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 3.0 g of [5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrophenyl]isopropyl sulfide (yield 90.0%) as a yellow dough (nD20 1.5881).

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. extractionextracted with 50 ml of ethyl acetate twice
  4. washThe ethyl acetate was washed with 100 ml of water twice
  5. dry with materialdried out anhydrous magnesium sulfate
  6. distillationthe ethyl acetate was distilled off under reduced pressure
  7. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-be75bf905930436cbd951b46d01c7fee
Source dataset
uspto-grants-2006_05
Patent number
US07037930B2

Reaction notes

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