반응 #215829

반응 방정식

8-chlorodibenz[b,f][1,41oxazepine-10(11H)-carboxylic acid, hydrazide

3-(3-pyridyl) acrylic acid

N,N-diisopropylethylamine

ethyl acetate

→

8-chlorodibenz[b,f][1,4]oxazepine-10 (11H)-carboxylic acid, 2-[1-oxo-3-(3-pyridinyl)-2E-propenyl]hydrazide

용매

dimethyl formamide

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   기타The resulting layers were separated
3. 3
   세척the organic layer was washed three times with saturated KHCO3 and two times with water
4. 4
   건조The organic layer was then dried over Na2SO4 anhydrous
5. 5
   여과filtered
6. 6
   기타The solvent was removed under vacuum
7. 7
   기타the resultant solid was chromatographed

실험 절차

To a stirring solution of 2.82 g (9.7 mmol) of 8-chlorodibenz[b,f][1,41oxazepine-10(11H)-carboxylic acid, hydrazide (1), prepared as described above in Example 1, in 25 mL of dimethyl formamide (DMF) cooled in an ice bath was added 1.54 g (9.7 mmol) of 3-(3-pyridyl) acrylic acid. To the heterogenous mixture was added 1.74 mL (10 mmol) of N,N-diisopropylethylamine and 1.92 g (10 mmol) of N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The reaction was stirred over night at ambient temperature. To the reaction was added 100 mL of ethyl acetate (EtOAc) and 100 mL of a saturated solution of KHCO3. The resulting layers were separated, and the organic layer was washed three times with saturated KHCO3 and two times with water. The organic layer was then dried over Na2SO4 anhydrous and filtered. The solvent was removed under vacuum, and the resultant solid was chromatographed. The yield of isolated product was 2.16 g (53%). Analysis calculated for C22H17N4O3Cl (M.W. 420.86): C, 62.79; H, 4.07; N, 13.31; Cl, 8.42. Found: C, 62.72; H, 4.27; N, 12.78; Cl, 8.21.

출처