2-Naphthoic acid → 2-Naphthalenecarbonyl isothiocyanate

To a mixture of 2-naphthyl carboxylic acid (5.0 g, 29.0 mmol) and 2 drops of N,N'-dimethylformamide in dry tetrahydrofuran (50 ml) was added dropwise thionyl chloride (6.3 ml, 87 mmol) and the resulting reaction mixture was stirred at reflux temperature for 3 h. The volatiles were evaporated in vacuo and the solid residue was redissolved in dry tetrahydrofuran (30 ml) and added dropwise to a solution of potassium thiocyanate (2.9 g, 30 mmol) in acetone (40 ml). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with water (250 ml) and extracted with diethyl ether (2×100 ml). The combined organic extracts were washed with saturated aqueous sodium chloride (2×80 ml), dried (MgSO4), filtered and evaporated in vacuo affording 5.2 g (84%) of naphthalene-2-carbonyl isothiocyanate.

1. customthe resulting reaction mixture
2. temperatureat reflux temperature for 3 h
3. customThe volatiles were evaporated in vacuo
4. dissolutionthe solid residue was redissolved in dry tetrahydrofuran (30 ml)
5. stirringThe reaction mixture was stirred at room temperature for 16 h
6. customThe reaction mixture was quenched with water (250 ml)
7. extractionextracted with diethyl ether (2×100 ml)
8. washThe combined organic extracts were washed with saturated aqueous sodium chloride (2×80 ml)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customevaporated in vacuo

ORD record

ord-62d97194fc01438ab9085bedb0797a81

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05958957