2,3-Dihydroxybutanedioic Acid → HCID 22961516, compound

HRID 2304752Notes

Reaction equation

HRID 2304752 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:8](O)(=[O:16])[CH:9]([CH:11]([C:13](O)=[O:14])[OH:12])[OH:10]>C1(C)C=CC=CC=1>[CH2:1]([N:7]1[C:13](=[O:14])[CH:11]([OH:12])[CH:9]([OH:10])[C:8]1=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic Acid2×HCID 8102Hexylamine2×

Product 1

HCID 22961516HCID 22961516, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

N-hexyl DL-tartarimide was prepared by the reaction of n-hexyl amine with DL-tartaric acid. DL-Tartaric acid (10.026 g, 66.80 mmole) and toluene (17.327 g) 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 n-hexyl amine (6.760 g, 66.80 mmole) and toluene (7.936 g, 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-d5d6b11af74647cbb5a791baac75f877
Source dataset
uspto-grants-2002_08
Patent number
US06437009B1

Reaction notes

Loading…