تفاعل #480753

معادلة التفاعل

Diethylaniline

1-Naphthoic acid

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

1-hydroxybenzotriazole

→

naphthalene-1-carboxylic acid amide

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىat 0° C
2. 2
   أخرىwas quenched with saturated aqueous ammonium chloride solution (3 mL)
3. 3
   workup.ADDITIONThe mixture was diluted with ethyl acetate (10 mL)
4. 4
   أخرىthe layers were separated
5. 5
   استخلاصThe aqueous layer was extracted with ethyl acetate (10 mL)
6. 6
   تجفيفthe combined organic layer was dried over sodium sulfate
7. 7
   تركيزConcentration in vacuo
8. 8
   workup.WAITleft a white solid, which
9. 9
   أخرىwas purified by flash column chromatography (80% ethyl acetate-hexanes)

الإجراء التجريبي

Diethylaniline (0.27 μL, 1.7 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (0.8 mg, 1.5 μmol, 1 equiv) in THF (0.2 mL) at 0° C. under an argon atmosphere and the solution was stirred for 5 min. 1-Naphthoic acid (0.34 mg, 2.0 μmol, 1.3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.38 mg, 2.0 μmol, 1.3 equiv) and 1-hydroxybenzotriazole (0.25 mg, 1.8 μmol, 1.2 equiv) were then added separately, each in one portion, to the above solution at 0° C. The reaction mixture was warmed to 23° C. over 14 h 45 min, then was quenched with saturated aqueous ammonium chloride solution (3 mL). The mixture was diluted with ethyl acetate (10 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layer was dried over sodium sulfate. Concentration in vacuo left a white solid, which was purified by flash column chromatography (80% ethyl acetate-hexanes) to give the naphthalene-1-carboxylic acid amide derivative (0.7 mg, 68%) as a white solid.

المصدر