Maleic Anhydride → (2Z)-4-(Cyclohexylamino)-4-oxo-2-butenoic acid

HRID 232341Notes

Reaction equation

HRID 232341 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C1(C)C=CC=CC=1>[CH:8]1([NH:14][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 7965Cyclohexylamine

Product 1

HCID 1551599(2Z)-4-(Cyclohexylamino)-4-oxo-2-butenoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 98 g of maleic anhydride in 500 g of toluene, 99.2 g of cyclohexylamine was added dropwise at a temperature in the range of 50° to 70° C. while in a stirred state. After the dropwise addition, the resultant mixture was stirred for two hours. Consequently N-cyclohexyl maleinamic acid was obtained. Then, the reaction solution and 14 g of methanesulfonic acid, 8.7 g of methanesulfonic acid-N-cyclohexyl maleinamate, and 15 g of N-methyl pyrrolidone added thereto were left reacting at 115° C. for 3.5 hours in a refluxed state, with the formed water continuously expelled from the reaction system through azeotropic distillation with toluene.

Workup

  1. additionAfter the dropwise addition

Sources & evidence

ORD record
ord-eda93825779e4ae58b11266d0d352434
Source dataset
uspto-grants-1989_07
Patent number
US04851547

Reaction notes

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