Dichloromethane → Methyl(1-naphthyl)cyanamide

In a 2 neck round bottom flask, equipped with a magnetic stir bar and reflux condenser, was placed N,N-dimethyl-1-naphthylamine (4.35 g, 25.4 mmol, and BrCN (2.99 g, 28.2 mmol) in a single portion. This suspension was placed in an oil bath (preheated, 90° C.) and allowed to stir and reflux under N2 for 21 hours. During this time a gas was given off, detected by bubbler placed over the reflux condenser. The reaction was followed by TLC, using methylene chloride as the solvent and viewed under UV. After the 21 hours, the mixture was cooled, 100 ml of ether was added and the insoluble quaternary salt (669 mg) was filtered off. The ether filtrate was extracted with an aqueous 5M HCl solution (4×, 30 ml) and washed with water (5×, 20 ml). The ether was dried over anhydrous granular K2CO3, filtered, then concentrated to dryness, then distilled by bulb to bulb distillation at reduced pressure to afford the yellow oil of the N-methyl-N-(1-naphthyl)cyanamide (2.22 g, 48%. b.p. 180° C./1.5 mm Hg (Cressman, Homer, W. J., Org. Synth. collective vol.3, 608), 170°-171° C./1 mm Hg).

1. customIn a 2 neck round bottom flask, equipped with a magnetic stir bar
2. temperaturereflux condenser
3. customThis suspension was placed in an oil bath
4. custom(preheated, 90° C.)
5. temperaturereflux under N2 for 21 hours
6. temperatureAfter the 21 hours, the mixture was cooled
7. filtrationthe insoluble quaternary salt (669 mg) was filtered off
8. extractionThe ether filtrate was extracted with an aqueous 5M HCl solution (4×, 30 ml)
9. washwashed with water (5×, 20 ml)
10. dry with materialThe ether was dried over anhydrous granular K2CO3
11. filtrationfiltered
12. concentrationconcentrated to dryness
13. distillationdistilled by bulb to bulb distillation at reduced pressure

ORDレコード

ord-22a219c91a524e32839d1d9533ad4a46

出典データセット

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05798390