Cyclohexylamine → N-cyclohexyl-2-nitro-4-(trifluoromethyl)aniline

HRID 1458795Notes

Reaction equation

HRID 1458795 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH:15]1([NH:21][C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium Carbonate

Product 1

HCID 3853727N-cyclohexyl-2-nitro-4-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 50 g (0.22 mol) of 2-nitro-4-trifluoromethyl-1-chlorobenzene, 22 g (0.22 mol) of cyclohexylamine and 61 g (0.44 mol) of potassium carbonate in 600 ml of ethanol was refluxed for 4 hours. The reaction mixture was concentrated and then the crude product was washed with water and ether. The organic phase was worked up, and the product was purified by column chromatography on silica gel (mobile phase:heptane/ethyl acetate=5/1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe crude product was washed with water and ether
  3. customthe product was purified by column chromatography on silica gel (mobile phase:heptane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f366be7ff8a747a8be6fcef07593bbff
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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