Hydrochloric Acid → (2Z)-4-(Dodecylamino)-4-oxo-2-butenoic acid

HRID 1418106Notes

Reaction equation

N1C=CC=CC=1.[C:7]1(=[O:13])[O:12][C:10](=[O:11])[CH:9]=[CH:8]1.[CH2:14]([NH2:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>ClCCl>[CH2:14]([NH:26][C:7](=[O:13])/[CH:8]=[CH:9]\[C:10]([OH:12])=[O:11])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 25 °C

Procedure

30 g of pyridine are added to a solution of 83 g of maleic anhydride in 700 ml of dichloromethane at room temperature. A solution of 122 g of n-dodecyl-amine and 70 g of pyridine in 800 ml of dichloro-methane is then added dropwise in 15 min, during which the temperature rises to 39° C. The mixture is then refluxed for 30 min, cooled to 25° C. and 210 ml of 32% by weight aqueous hydrochloric acid are cautiously added. The aqueous phase is separated off at 35° C., and the organic phase is washed three times with 200 ml of water each time at 35° C., dried over sodium sulfate and crystallized at 10° C. 180 g (96%) of N-dodecylmaleamic acid are obtained in the form of colorless waxy crystals. The product is pure by NMR and gives a clear solution in dilute sodium hydroxide solution.

Workup

customrises to 39° C
temperatureThe mixture is then refluxed for 30 min
customThe aqueous phase is separated off at 35° C.
washthe organic phase is washed three times with 200 ml of water each time at 35° C.
dry with materialdried over sodium sulfate
customcrystallized at 10° C

Sources & evidence

ORD record: ord-6fbe1313940e428cbe5e5d05c6034a94
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880236

Reaction notes

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