Water → 4-(Cyclohexylamino)-3-nitrobenzonitrile

HRID 1709217Notes

Reaction equation

HRID 1709217 reaction equation
Cl[C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)C#N.[CH2:13]([N:15](CC)CC)C.[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>CN(C)C=O>[CH:20]1([NH:26][C:2]2[CH:9]=[CH:8][C:7]([C:13]#[N:15])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 218758793-Chloro-2-nitrobenzonitrile

Product 1

HCID 29852004-(Cyclohexylamino)-3-nitrobenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3.0 g (16 mmol) 3-chloro-2-nitrobenzonitrile in 50 ml dimethylformamide was added 1.8 g (18 mmol) dry triethylamine and 1.8 g (18 mmol) cyclohexylamine. The reaction mixture was stirred at 80° C. for 1 h. After cooling to 25° C. 100 ml water was added, and the precipitate was filtered off. The crude product was recrystallized (methanol) to give 1.6 g (65%) N-cyclohexyl-4-cyano-2-nitroaniline. M.p. 109.0° C. 1H-NMR (CDCl3): 8.4-6.8 (4H, m), 3.5 (1H, broad s), 2.4-1.0 (10H, m).

Workup

  1. temperatureAfter cooling to 25° C
  2. filtrationthe precipitate was filtered off
  3. customThe crude product was recrystallized (methanol)

Sources & evidence

ORD record
ord-b0a672bb67d74c5a96dffb06d95f2bc2
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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