ISOXAZOLIDINE HYDROCHLORIDE Chemical Properties

Melting point:

125.0 to 129.0 °C

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

color 

White to Almost white

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

ISOXAZOLIDINE HYDROCHLORIDE Usage And Synthesis

Uses

Isoxazolidine Hydrochloride is used to form isoxazolidides by high yield acylation.

Synthesis

The general procedure for the synthesis of isoxazolidine hydrochloride from 1,3-dichloropropane was as follows: first, 1,3-dichloropropane (1.6 mL, 15 mmol, 1.2 eq.) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene; 1.8 mL, 12 mmol, 1.0 eq.) were sequentially added to a stirring solution of 2-hydroxyisoindoline-1,3 -dione (N-hydroxyphthalimide; 2.0 g, 12 mmol, 1.0 eq.) in a solution of DMF (30 mL) at a reaction temperature of 23 °C. The reaction mixture was heated to 50 °C and stirred continuously for 18 hours. Upon completion of the reaction, the resulting colorless solution was diluted with 1 M aqueous HCl (300 mL) and extracted with ether (Et2O; 2 x 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), gravity filtered and concentrated by rotary evaporation to give a colorless oil (1.5 g). The oil was dissolved in ethanol (EtOH; 15 mL), hydrazine hydrate (300 μL, 11 mmol, 1.0 eq.) was added, and the light yellow suspension was stirred at 23 °C for 4 h. The reaction mixture was filtered under vacuum. The reaction mixture was filtered under vacuum and the filtrate was concentrated by rotary evaporation to give a light yellow powdery product (530 mg, 77% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 5.34 (broad single peak, 2H), 4.07 (triple peak, J = 7 Hz, 2H), 3.37 (triple peak, J = 7 Hz, 2H), 2.30 (quintuple peak, J = 7 Hz, 2H).

References

[1] Patent: US2010/222221, 2010, A1. Location in patent: Page/Page column 7

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