Dimethylmaleic anhydride → N-(4-hydroxycyclohexyl)-dimethylmaleimide

HRID 1701485Notes

Reaction equation

HRID 1701485 reaction equation
[CH3:1][C:2]1=[C:3]([CH3:9])[C:4]([O:6][C:7]1=[O:8])=O.[NH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1>C(Cl)Cl>[OH:17][CH:14]1[CH2:15][CH2:16][CH:11]([N:10]2[C:4](=[O:6])[C:3]([CH3:9])=[C:2]([CH3:1])[C:7]2=[O:8])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 812934-Aminocyclohexanol

Product 1

HCID 20346782N-(4-hydroxycyclohexyl)-dimethylmaleimideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

126 g (1 mol) of dimethylmaleic anhydride and 115 g (1 mol) of 4-aminocyclohexanol are warmed, whilst stirring, to 120°-125° C. (internal temperature) for 30 minutes in an oil bath. After cooling to about 20° C., the reaction product is dissolved in 500 ml of methylene chloride and the solution is extracted once with 100 ml of 1 N NaOH, whilst cooling with ice. The reaction product is then washed twice with water and dried over Na2SO4. The solvent is evaporated and the residue is recrystallised from a 1:1 mixture by volume of ethyle acetate and petroleum ether. 155 g (70% of theory) of N-(4-hydroxycyclohexyl)-dimethyl-maleimide are obtained; melting point 109°-111° C.

Workup

  1. extractionthe solution is extracted once with 100 ml of 1 N NaOH
  2. temperaturewhilst cooling with ice
  3. washThe reaction product is then washed twice with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent is evaporated
  6. customthe residue is recrystallised from a 1:1 mixture by volume of ethyle acetate and petroleum ether

Sources & evidence

ORD record
ord-bed6d20f1dce49ccb2bb78aa230ec440
Source dataset
uspto-grants-1980_03
Patent number
US04193927

Reaction notes

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