Chloroacetyl chloride → 5-Chloromethyl-3-naphthalen-2-yl-[1,2,4]oxadiazole

Temperature

50 °C

A solution of N-Hydroxy-naphthalene-2-carboxamidine (364 mg, 1.95 mmol) in dichloroethane (6 mL) and DIEA (683 μL, 3.91 mmol) was treated with a solution of chloroacetyl chloride (157 μL, 2.350 mmol) in dichloroethane (2 mL) which was added dropwise to the reaction vessel at room temperature. After the addition, the reaction mixture was heated at 50° C. for 4 hours. The reaction mixture was then concentrated to dryness and redissolved in dichloromethane. The organic layer was washed with saturated aqueous NaHCO3 and brine, respectively. The organic layer was dried over anhydrous Na2SO4, concentrated onto silica gel and purified by flash chromatography (0-50% ethyl acetate/hexanes gradient) to afford the required intermediate, 5-chloromethyl-3-naphthalen-2-yl-[1,2,4]oxadiazole (102 mg).

1. additionwas added dropwise to the reaction vessel at room temperature
2. additionAfter the addition
3. concentrationThe reaction mixture was then concentrated to dryness
4. dissolutionredissolved in dichloromethane
5. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. concentrationconcentrated onto silica gel
8. custompurified by flash chromatography (0-50% ethyl acetate/hexanes gradient)

ORD record

ord-2eaf408525ce45c39b0103b37169fa96

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315449B2