2,5-Furandione, 3,4-dibromo- → HCID 178446516, compound

HRID 1380572Notes

Reaction equation

HRID 1380572 reaction equation
[Br:1]/[C:2](/[C:8]([OH:10])=[O:9])=[C:3](\[Br:7])/[C:4](O)=[O:5].[CH2:11]([CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][CH2:15][NH2:16])[CH3:12].BrC1=C(Br)C(OC1=O)=O>C(O)(=O)C>[C:17]1([CH:13]([CH2:11][CH3:12])[CH2:14][CH2:15][N:16]=[C:4]([OH:5])/[C:3](/[Br:7])=[C:2](/[Br:1])\[C:8]([OH:10])=[O:9])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 707272,5-Furandione, 3,4-dibromo-HCID 27238962-Butenedioic acid, 2,3-dibromo-, (2Z)-HCID 132903133-Ethyl-3-phenyl-propylamine

Product 1

HCID 178446516HCID 178446516, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

14 g (0.051 mol) of dibromomaleic acid are stirred in 100 ml of glacial acetic acid under reflux for 1 hour. 8.2 g (0.05 mol) of 3-ethyl-3-phenyl-propylamine are added to the cooled solution of the dibromomaleic anhydride thus prepared, and the mixture is stirred under reflux for a further 3 hours. The mixture is cooled to 20° C. and the precipitate is filtered off with suction. After drying, 11.4 g (56% of theory) of dibromomaleic acid N-3-phenylpentylimide of melting point 71°-73° C. are obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. customthus prepared
  3. temperatureunder reflux for a further 3 hours
  4. filtrationthe precipitate is filtered off with suction
  5. customAfter drying

Sources & evidence

ORD record
ord-b496e5699d99464ba3e40cdb188f5ec4
Source dataset
uspto-grants-1986_04
Patent number
US04582849

Reaction notes

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