Malic Acid → HCID 131723443, compound

HRID 2304753Notes

Reaction equation

HRID 2304753 reaction equation
C([CH:3](CCCC)[CH2:4][NH2:5])C.[C:10]([OH:18])(=O)[CH:11]([CH2:13][C:14]([OH:16])=O)[OH:12].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21]C=1>>[CH3:3][CH2:4][N:5]1[C:14](=[O:16])[CH2:13][C:11]([CH2:25][CH2:19][CH2:24][CH2:23][CH2:22][CH3:21])([OH:12])[C:10]1=[O:18]

Participants

4

Reactant 3

HCID 525Malic Acid2×HCID 1140Toluene2×HCID 77192-Ethylhexylamine2×

Product 1

HCID 131723443HCID 131723443, compound

Conditions

Temperature
100 °C

Procedure

N-2-Ethylhexyl DL-malimide was prepared by the reaction of 2-ethylhexyl amine with DL-malic acid. DL-Malic acid (10.327 g, 77.015 mmole) and toluene (40 mL) were weighed into a 250 mL 3-necked round-bottomed flask equipped with a teflon-coated magnetic stir bar. A Claisen adapter was placed in the center neck, a Dean-Stark trap was placed on top of the Claisen adapter, and a condenser was placed in the neck of the Dean-Stark trap. A nitrogen inlet adapter was placed on the condenser. In the left neck was placed a pressure-equalizing addition funnel containing 2-ethylhexyl amine (9.955 g, 77.02 mmole) and toluene (10 mL, added to ensure complete transfer of the amine). In the right neck was placed a rubber septum which held a thermocouple. The apparatus was purged with nitrogen for 10-15 minutes and then heated to ˜100° C.

Workup

  1. customequipped with a teflon-coated magnetic stir bar
  2. customA nitrogen inlet adapter was placed on the condenser
  3. additiona pressure-equalizing addition funnel
  4. additionadded
  5. customThe apparatus was purged with nitrogen for 10-15 minutes

Sources & evidence

ORD record
ord-0ce9d8bc85bd4c578b5e1bc65da6f803
Source dataset
uspto-grants-2002_08
Patent number
US06437009B1

Reaction notes

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