Maleic Anhydride → (2Z)-4-(Hexadecylamino)-4-oxo-2-butenoic acid

HRID 1155319Notes

Reaction equation

HRID 1155319 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:24])[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][CH3:23]>C1(C)C=CC=CC=1>[CH2:8]([NH:24][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][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 8926Hexadecylamine

Product 1

HCID 21116159(2Z)-4-(Hexadecylamino)-4-oxo-2-butenoic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

19.6 g of maleic acid anhydride are dissolved in 500 ml of toluene at 90° C. The temperature is maintained at 90° C. while 48.2 g of hexadecylamine, dissolved in 200 ml of toluene are added dropwise within 45 minutes. After one more hour at 90° C. followed by cooling, the resulting precipitate is suction filtered and washed with methanol. 44.5 g of N-hexadecylmaleic amide melting at 101° to 102.5° C. are obtained.

Workup

  1. additionare added dropwise within 45 minutes
  2. customat 90° C.
  3. temperatureby cooling
  4. filtrationfiltered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-f11e99bd6ac845bd9bb592ce936c4536
Source dataset
uspto-grants-1981_11
Patent number
US04301243

Reaction notes

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