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

HRID 128485
Notes
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Reaction equation

HRID 128485 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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 L 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-f80b141f54f940a7864c26280652765b
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04259510

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes