Triethylamine → 5-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide

To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.7 g, 3.76 mmol) in isopropanol (40 ml) was added triethylamine (630 μl, 4.51 mmol) and diphenyl cyanocarbonimidate (0.99 g, 4.14 mmol) and the resulting reaction mixture was stirred at room temperature for 1.5 h. The volatiles were evaporated in vacuo and to the residue was added water (50 ml) and diethyl ether (50 ml). The organic phase was separated and the aqueous phase was acidified to pH=1 with concentrated hydrochloric acid. The precipitate was filtered off and washed with water (3×10 ml) and diethyl ether (2×10 ml) and dried in vacuo at 50° C. which afforded 0.45 g (51%) of the title compound as a solid.

1. customthe resulting reaction mixture
2. customThe volatiles were evaporated in vacuo and to the residue
3. additionwas added water (50 ml) and diethyl ether (50 ml)
4. customThe organic phase was separated
5. filtrationThe precipitate was filtered off
6. washwashed with water (3×10 ml) and diethyl ether (2×10 ml)
7. customdried in vacuo at 50° C. which

ORD record

ord-aa8283b3d06042a8930d331c4b2605d8

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06063800