Dimethyl Sulfoxide → 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide

HRID 444024Notes

Reaction equation

HRID 444024 reaction equation
CS(C)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22].F[C:24]1[CH:25]=[CH:26][C:27]([N+:33]([O-:35])=[O:34])=[C:28]([CH:32]=1)[C:29]([NH2:31])=[O:30]>O>[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:13]=1[O:22][C:24]1[CH:25]=[CH:26][C:27]([N+:33]([O-:35])=[O:34])=[C:28]([CH:32]=1)[C:29]([NH2:31])=[O:30]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 27366032-Chloro-4-(trifluoromethyl)phenolHCID 186681655-Fluoro-2-nitrobenzamide

Product 1

HCID 153350195-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzamideYield 13.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml flask fitted with a magnetic stirrer and drying tube is added dimethyl sulfoxide (50 ml), anhydrous potassium carbonate (3.6 g, 0.026 mole) and 2-chloro-4-trifluoromethylphenol (4.8 g, 0.024 mole). This mixture is stirred at room temperature overnight. 5-Fluoro-2-nitrobenzamide (4.5 g, 0.024 mole) is added rapidly and the reaction mixture stirred at room temperature for 24 hours. The reaction mixture is poured into water (300 ml) and triturated with carbon tetrachloride (50 ml). The water and carbon tetrachloride insoluble solid is collected by filtration and dried under vacuum to afford 1.2 g of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide, mp 139°-43° C. Anal. Calcd. for C14H8ClF3N2O4 : C, 46.62; H, 2.23; Cl, 9.83; N, 7.76. Found: C, 45.77; H, 2.30; Cl, 10.62; N, 7.91.

Workup

  1. customTo a 100 ml flask fitted with a magnetic stirrer
  2. customdrying tube
  3. stirringthe reaction mixture stirred at room temperature for 24 hours
  4. customtriturated with carbon tetrachloride (50 ml)
  5. filtrationThe water and carbon tetrachloride insoluble solid is collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e3d4a52f80c54976b5a67e1a0b5638c5
Source dataset
uspto-grants-1981_04
Patent number
US04262152

Reaction notes

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