Hydrochloric Acid → HCID 86747141, compound

HRID 2379289Notes

Reaction equation

HRID 2379289 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[C:22]1(=[O:28])[O:27][C:25](=[O:26])[CH:24]=[CH:23]1.Cl>C(O)C.[OH-].[Na+]>[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26])([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 15232942HCID 15232942, compound

Product 1

HCID 86747141HCID 86747141, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

In a mixture of 50 ml of ethanol and 25 ml of 1N aqueous sodium hydroxide solution, 18-aminooctadecanoic acid (400 mg, 1.33 mmoles) was dissolved at 40° C. To the obtained solution, being maintained at 40° C., was gradually added maleic anhydride (1.97 g, 20.0 mmoles) over a period of 2 hours. The reaction mixture was stirred for 30 minutes, then acidified with hydrochloric acid under ice-cooled condition and subjected to centrifugation. The precipitate was collected by filtration, sufficiently washed with water and then dried under reduced pressure, to give N-(17-carboxyheptadecyl)maleamic acid (436 mg, 88%) having the following properties.

Workup

  1. dissolutionwas dissolved at 40° C
  2. customof 2 hours
  3. temperaturecooled condition
  4. filtrationThe precipitate was collected by filtration
  5. washsufficiently washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-84e5d7cefe6142918b8ab0275d567369
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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