Succinic anhydride → HCID 86650123, compound

Temperature

40 °C

Succinic anhydride (23.0 g, 0.230 mol) was added into a three-neck round-bottom flask equipped with a condenser and a dropping funnel. Under nitrogen atmosphere and magnetic stirring, freshly distilled methylene chloride (150 mL), DMAP (2.3 g, 19 mmol) and freshly distilled Et3N (46.46 g, 0.460 mol) was sequentially added. After the flask was immersed into an ice-water bath, 2-azidoethanol (20.0 g, 0.230 mol) was added dropwise into the previous solution. The solution was later heated at 40° C. for 48 h, and the reaction mixture was washed successively with 1 M HCl solution (5×100 mL) and deionized water (2×100 mL). The organic phase was dried over anhydrous MgSO4 overnight. After filtering and removal of methylene chloride under reduced pressure, the final product was obtained as a yellow viscous liquid. The yield was: 38.4 g, 90%. 1H NMR (CDCl3, δ, ppm): 4.20 (t, 2H, N3CH2CH2), 3.42 (t, 2H, N3CH2), and 2.61 (m, 4H, CH2CH2COOH).

1. customequipped with a condenser and a dropping funnel
2. customAfter the flask was immersed into an ice-water bath
3. washthe reaction mixture was washed successively with 1 M HCl solution (5×100 mL) and deionized water (2×100 mL)
4. dry with materialThe organic phase was dried over anhydrous MgSO4 overnight
5. filtrationAfter filtering
6. customremoval of methylene chloride under reduced pressure

ORD record

ord-a877f90dcfe541f5a4bc376794e8ac0e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08986515B2