Maleic Anhydride → HCID 86747143, compound

HRID 2379298Notes

Reaction equation

HRID 2379298 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][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH:28]=[CH:27]1>C(O)C.[OH-].[Na+]>[C:23]([CH2:22][CH2:21][CH2:20][CH2:19][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:26](=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30])([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 7923Maleic AnhydrideHCID 18958350HCID 18958350, compound

Product 1

HCID 86747143HCID 86747143, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

In a mixture of 100 ml of ethanol and 50 ml of 1N aqueous sodium hydroxide solution, 22-aminodocosanoic acid (400 mg, 1.12 mmoles) was dissolved at 40° C. To the obtained solution, the temperature being maintained at 40° C., maleic anhydride (4.39 g, 44.8 mmoles) was gradually added over a period of 5 hours. The reaction mixture was kept at a pH of 8-10 during the addition, and the mixture was stirred for additional 30 minutes and then treated in the same manner as in Reference Example 4, to give N-(21-caboxyheneicosyl)maleamic acid (538 mg, 83%) having the following properties.

Workup

  1. dissolutionwas dissolved at 40° C
  2. additionThe reaction mixture was kept at a pH of 8-10 during the addition
  3. additiontreated in the same manner as in Reference Example 4

Sources & evidence

ORD record
ord-8b16457d4b6b46f2a2caceb5754c4193
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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