Nitric Acid → 5-Chloro-2-ethoxalylamino-3-nitrobenzotrifluoride

HRID 346128Notes

Reaction equation

HRID 346128 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:14])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-:22])=[O:21])[C:5]([NH:12][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:14])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4550962Ethyl 2-[4-chloro-2-(trifluoromethyl)anilino]-2-oxoacetate

Product 1

HCID 199803055-Chloro-2-ethoxalylamino-3-nitrobenzotrifluorideYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 2.4 g (8.1 mmol) 5-chloro-2-ethoxalylaminobenzotrifluoride in 13 ml 95-97% sulfuric acid a solution of 12 ml 100% nitric acid in 24 ml 95-97% sulfuric acid was added dropwise at 0°-5° C. Stirring was continued at 25° C. for 20 min. The reaction mixture was poured into 100 ml ice-water to give an oil. Extraction with dichloromethane gave 2.1 g (76%) of 5-chloro-2-ethoxalylamino-3-nitrobenzotrifluoride as crystals. M.p. 100°-101° C.

Workup

  1. customto give an oil
  2. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-c9c2ccc2d5cb402cb46c594424500cb2
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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