Water → 4-chloro-N-cyclohexyl-2-nitroaniline

HRID 861499Notes

Reaction equation

HRID 861499 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:18][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 69772,5-DichloronitrobenzeneHCID 7965CyclohexylamineHCID 11430Potassium Carbonate

Product 1

HCID 28372924-chloro-N-cyclohexyl-2-nitroanilineYield 62%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

51.5 g (0.27 mol) of 2,5-dichloronitrobenzene, 22.3 g (0.27 mol) of cyclohexylamine, 74.6 g (0.54 mol) of potassium carbonate and 0.5 g of 18-crown-6 in 300 ml of dimethylformamide were heated at 100° C. for 4 h. The mixture was then poured into water and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was recrystallized from i-propanol, resulting in 42.3 g (62%) of the product. Melting point 101°-103° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from i-propanol

Sources & evidence

ORD record
ord-62ac12952cee4a26bd2151beaa03859d
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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