Succinic anhydride → HCID 19702838, compound

HRID 861301Notes

Reaction equation

HRID 861301 reaction equation
[OH:1][CH:2]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>CCOCC>[CH2:13]([N:12]([CH2:11][CH:2]([OH:1])[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 19702843HCID 19702843, compound

Product 1

HCID 19702838HCID 19702838, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reactor was charged with 20 g (0.053 mole) of 9-hydroxy-7,11-diaza-tricosane, 13 g (0.130 mole) of succinic anhydride and 300 ml of anhydrous ether, and the contents were refluxed for 5 hours. After completion of a reaction, insoluble succinic anhydride in an excess amount was removed by filtration, and an ether layer was washed with water. The ether was distilled off under reduced pressure, thereby obtaining 30 g (0.055 mole) of 4-dodecyl-8-hexyl-3,9-dioxo-6-hydroxy-4,8-diaza-1,11-undecanedicarboxylic acid as a viscous transparent liquid. After adjusted to pH 10 with sodium hydroxide, this compound gave a single peak in HPLC measurement [column: RP-18 (product of Merck Co.), eluent: methanol/water=80/20]. The 1 H-NMR data of the compound will be shown below.

Workup

  1. temperaturethe contents were refluxed for 5 hours
  2. customwas removed by filtration
  3. washan ether layer was washed with water
  4. distillationThe ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8e2cb170a7fe492a9ee9f8864c6b3ac3
Source dataset
uspto-grants-1998_02
Patent number
US05714457

Reaction notes

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