Reaction #468878

ord-1810b883c02e425693ad127b2e15a4b3

Reaction equation

CCCCC(CC)CO
2-ethylhexanol
NC(=O)N1C(=O)C=CC1=O
N-carbamylmaleimide
→
CCCCC(CC)COC(=O)/C=C\C(=O)NC(N)=O
2-ethylhexyl maleurate
Yield 95.0%

Reactants

CCCCC(CC)CO
2-ethylhexanol
NC(=O)N1C(=O)C=CC1=O
N-carbamylmaleimide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The addition of 2-ethylhexanol to N-carbamylmaleimide under the conditions of Example C afforded a 95% yield of 2-ethylhexyl maleurate. M.P.: 73°-6° C.; 1H NMR (CDCl3): δ10.6 (br s, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.8 (br s, 1H), 4.2 (m, 2H), 1.6 (m, 1H), 1.3 (m, 8H), 0.9 (t, 6H); HPLC (40% CH3CN/H2O, C8): Rt=14.2 minutes.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06307058B1uspto-grants-2001_10