Cyclohexylamine → HCID 22165184, compound

HRID 1032232Notes

Reaction equation

HRID 1032232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:11][C:12](=[O:14])[CH:13]=1)=O.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)(=O)C>[CH:15]1([N:21]2[C:12](=[O:14])[CH:13]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]2=[O:11])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 12290224HCID 12290224, compound

Product 1

HCID 22165184HCID 22165184, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(2-chlorophenyl)maleic anhydride (125.0 g) in acetic acid (1.2 1) is added cyclohexylamine (59.4 g) and the mixture is refluxed for 12 hours. The solvent is distilled off and the residue is dissolved in ethyl acetate (500 ml). This solution is successively washed with 5% hydrochloric acid (150 ml), sodium hydrogen carbonate solution (500 ml) and water (150 ml) and dried over magnesium sulfate. The solvent is distilled off and the residue is distilled off to give N-cyclohexyl-(2-chlorophenyl)maleimide (oil) (90.2 g), b.p. 171°-176° C./0.8 ton.

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. distillationThe solvent is distilled off
  3. dissolutionthe residue is dissolved in ethyl acetate (500 ml)
  4. washThis solution is successively washed with 5% hydrochloric acid (150 ml), sodium hydrogen carbonate solution (500 ml) and water (150 ml)
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off
  7. distillationthe residue is distilled off

Sources & evidence

ORD record
ord-16d6e4cc9cdb40cc8dc22390fa6613a8
Source dataset
uspto-grants-1990_09
Patent number
US04957537

Reaction notes

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