Maleic Anhydride → HCID 86748487, compound

HRID 275477Notes

Reaction equation

HRID 275477 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)(Cl)(Cl)Cl>[CH2:8]([NH:30][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 2084136813-Docosen-1-amine, (13Z)-

Product 1

HCID 86748487HCID 86748487, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A 250 ml, 3-neck flask equipped with a stirrer, thermometer, Dean-Stark receiver and condenser was charged with 18 g of maleic anhydride (0.18 mole) and 60 ml carbon tetrachloride. Erucyl amine (59.0 g, 0.18 mole) was added dropwise at 70° C. under a nitrogen atmosphere. The mixture was stirred at 75° C. for 4 hours. The temperature was raised to 90° C. to distill out carbon tetrachloride and the mixture was then stripped at 100° C. 10 mmHg vacuum for 15 minutes to afford 73 g of N-Erucyl-maleic acid monoamide. An IR spectrum indicated the presence of amide and carboxyl groups. This product had an acid number of 135; no total amine value; a saponification value of 137.6; a melting point of 55° C.

Workup

  1. customA 250 ml, 3-neck flask equipped with a stirrer
  2. temperatureThe temperature was raised to 90° C.
  3. distillationto distill out carbon tetrachloride
  4. customwas then stripped at 100° C

Sources & evidence

ORD record
ord-e0ef28c12dca4c2382821b432ae8b3c6
Source dataset
uspto-grants-1995_02
Patent number
US05393814

Reaction notes

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