Acetic Acid → N-(2-cycloheptenyl)dichloromaleinimide

HRID 1461581Notes

Reaction equation

HRID 1461581 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Cl:9][C:10]1=[C:11]([Cl:17])[C:12]([O:14][C:15]1=O)=[O:13].C(O)(=O)C>CCOCC>[CH:1]1([N:8]2[C:15](=[O:14])[C:10]([Cl:9])=[C:11]([Cl:17])[C:12]2=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70728Dichloromaleic anhydrideHCID 11263481Cyclohept-2-en-1-amine

Product 1

HCID 13578660N-(2-cycloheptenyl)dichloromaleinimideYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-cycloheptenylamine (1.01 g), dichloromaleic anhydride (1.67 g) and acetic acid (10 ml) was heated under reflux for 3 hours. After cooling, ether (20 ml) was added to the reaction mixture which was then washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The deposited crystal was purified by recrystallization from hexane to obtain 1.67 g of N-(2-cycloheptenyl)dichloromaleinimide [Compound (217)].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. washwas then washed with a saturated aqueous sodium hydrogencarbonate solution, water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe deposited crystal was purified by recrystallization from hexane

Sources & evidence

ORD record
ord-3fe8d8d4080d46d2b084d219797d93be
Source dataset
uspto-grants-1991_12
Patent number
US05075488

Reaction notes

Loading…