Ethyl Acetate → HCID 19819658, compound

HRID 1030066Notes

Reaction equation

HRID 1030066 reaction equation
[Cl:1]Cl.[N+:3]([C:6]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:9]1[CH:10]=[C:11]([O:13][C:14]([F:15])([F:16])[F:17])[CH:12]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24526Chlorine2×HCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 19819658HCID 19819658, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Chlorine gas was passed through a solution of 2-nitro-4-trifluoromethoxy-aniline (14.5 g) in carbon tetrachloride (175 ml). As the mixture was stirred it became solid and more carbon tetrachloride (50 ml) was added. Chlorine gas was passed through the reaction mixture until thin layer chromatography (silica gel, using petroleum ether (boiling range 60°-80° C.) containing ethyl acetate (30% by volume) as eluent) demonstrated the absence of starting material. Evaporation of the solvent under reduced pressure gave a dark orange solid, which on trituration with petroleum ether (boiling range 60°-80° C.) gave a 2-chloro-4-trifluoromethoxy-6-nitro-aniline as an orange solid.

Workup

  1. additionwas added
  2. customEvaporation of the solvent under reduced pressure
  3. customgave a dark orange solid, which on trituration with petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-ea4db3e5fc9849bea3d0815c16b38809
Source dataset
uspto-grants-1992_04
Patent number
US05104878

Reaction notes

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