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

HRID 46603

反応式

HRID 46603 の反応式
[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

参加物

4

反応物 2

HCID 13010Dimethylmaleic anhydrideHCID 812934-Aminocyclohexanol

生成物 1

HCID 20346782N-(4-hydroxycyclohexyl)-dimethylmaleimide収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

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 recrystallized 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.

後処理

  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 recrystallized from a 1:1 mixture by volume of ethyle acetate and petroleum ether

出典と根拠

ORDレコード
ord-eaf52a7465754a36925234705843f923
出典データセット
uspto-grants-1979_11
特許番号
US04174326

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