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

HRID 1494346Notes

Reaction equation

HRID 1494346 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O>[CH:22]1([NH:28][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 8471Triethylamine

Product 1

HCID 3853727N-cyclohexyl-2-nitro-4-(trifluoromethyl)anilineYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5.0 g (22 mmol) 4-chloro-3-nitrobenzotrifluoride in 100 ml dimethylformamide was added 3.4 ml (24 mmol) triethylamine and 2.8 ml (23 mmol) cyclohexylamine. The reaction mixture was stirred at 80° C. for 2 h. After cooling to 25° C. the reaction mixture was evaporated in vacuo. The residue was stirred with 100 ml water and the precipitate was filtered off. Recrystallization (methanol) gave 3.9 g (61%) N-cyclohexyl-2-nitro-4-trifluoromethylaniline. M.p. 80.1° C., 1H-NMR (CDCl3): 8.4 (1H, s), 8.3 (1H, m), 7.5 (1H, dd), 6.9 (1H, d), 3.5 (1H, broad s).

Workup

  1. temperatureAfter cooling to 25° C. the reaction mixture
  2. customwas evaporated in vacuo
  3. stirringThe residue was stirred with 100 ml water
  4. filtrationthe precipitate was filtered off
  5. customRecrystallization (methanol)

Sources & evidence

ORD record
ord-d1f16d18be964cc3835b679bc85009e0
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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