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

HRID 972108Notes

Reaction equation

HRID 972108 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, in an oil bath whilst stirring, to 120° to 125° C. (internal temperature) for 30 minutes. After cooling to 20° C., the reaction product is dissolved in 500 ml of methylene chloride and 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 sodium sulphate. The solvent is evaporated and the residue is recrystallised from a 1:1 mixture by volume of ethyl acetate and petroleum ether. 155 g (70% of theory) of N-(4-hydroxycyclohexyl)-dimethylmaleimide are obtained; melting point 109° to 111° C.

Workup

  1. extractionextracted 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 sodium sulphate
  5. customThe solvent is evaporated
  6. customthe residue is recrystallised from a 1:1 mixture by volume of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-02aa968778624cd58fd352871f5b7272
Source dataset
uspto-grants-1979_07
Patent number
US04163097

Reaction notes

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