Ethanolamine → HCID 57267041, compound

HRID 1636470Notes

Reaction equation

[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.C(C[NH2:11])O.[C:12]([O:15][C:16](=[O:18])[CH3:17])(=O)[CH3:13].C([O-])(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(O)(=O)C>[C:16]([O:15][CH2:12][CH2:13][C:2]1[C:1]([NH:11][C:4](=[O:5])[CH:3]=1)=[O:7])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Maleic anhydride (172.32 g, 1.75 mol) was added to ethanolamine (107.34 g, 1.75 mol) and dissolved in 500 mL of acetone while stirring overnight in an ice bath. To the solution, 400 mL of acetic anhydride (4.23 mol) was added with sodium acetate (144 g, 1.75 mol). The solution was heated to 80° C. and stirred for 1 hour. The contents were poured into ice water and the acetic acid neutralized with K2CO3. The product was extracted with methylene chloride and then dried using magnesium sulfate. The product was purified by sublimation yielding white crystals, m.p. 76° C. (44.1 g, 13.45%) 1H-NMR (CDCl3, δ, ppm): 2.02 (3H, --CH3, s), 3.82-3.77 (2H, --NCH2 --, t), 4.25--4.20 (2H, --CH2O--, t), 6.75 (2H, --CH=CH--, s). 13C-NMR (CDCl3, δ, ppm): 20.7 (1C, --CH3), 37.0 (1C, --NCH2 --), 61.5 (1C, --CH2O--), 134.3 (2C, --CH=CH--), 170.5 (2C, --NC=O), 170.8 (1C, --OC=O).

Workup

stirringstirred for 1 hour
extractionThe product was extracted with methylene chloride
customdried
customThe product was purified by sublimation
customyielding white crystals, m.p. 76° C. (44.1 g, 13.45%) 1H-NMR (CDCl3, δ, ppm): 2.02 (3H, --CH3, s), 3.82-3.77 (2H, --NCH2 --, t), 4.25--4.20 (2H, --CH2O--, t), 6.75 (2H, --CH=CH--, s)

Sources & evidence

ORD record: ord-493d32ba311040078dd5d69e53ef3e0b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034150

Reaction notes

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