2,3-Dihydroxybutanedioic Acid → HCID 131723442, compound

HRID 2304750Notes

Reaction equation

HRID 2304750 reaction equation
C([CH:3](CCCC)[CH2:4][NH2:5])C.[C:10]([OH:19])(=O)[CH:11]([CH:13]([C:15]([OH:17])=O)[OH:14])[OH:12].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22]C=1>>[CH3:3][CH2:4][N:5]1[C:10](=[O:19])[CH:11]([OH:12])[C:13]([CH2:26][CH2:20][CH2:25][CH2:24][CH2:23][CH3:22])([OH:14])[C:15]1=[O:17]

Participants

4

Reactant 3

HCID 8752,3-Dihydroxybutanedioic Acid2×HCID 1140Toluene2×HCID 77192-Ethylhexylamine2×

Product 1

HCID 131723442HCID 131723442, compound

Conditions

Temperature
100 °C

Procedure

N-2-Ethylhexyl tartarimide was prepared by the reaction of 2-ethylhexyl amine with DL-tartaric acid. The procedure described in U.S. Pat. No. 4,237,022 was followed on a smaller scale. DL-Tartaric acid (10.034 g, 66.853 mmole) and toluene (17.328 g, 188.06 mmole) were weighed into a 250 mL 3-necked round-bottomed flask equipped with a teflon-coated magnetic stir bar. A Dean-Stark trap was placed in the center neck, 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 (8.639 g, 66.84 mmole) and toluene (6.092 g, 66.12 mmole) 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-397e2cde5d7948a9a0ca36afe74e7b45
Source dataset
uspto-grants-2002_08
Patent number
US06437009B1

Reaction notes

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