3-Nitrobenzaldehyde → 2-(n-Propoxy)ethyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate

HRID 247114

반응식

HRID 247114 반응식
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[C:2]([CH3:4])=O.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].[NH2:23]/[C:24](/[CH3:35])=[CH:25]\[C:26]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH3:34])=[O:27]>C(O)(C)C>[CH3:4][C:2]1[NH:23][C:24]([CH3:35])=[C:25]([C:26]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH3:34])=[O:27])[CH:18]([C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:1]=1[C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1

참가 물질

5

반응물 3

HCID 74493-NitrobenzaldehydeHCID 125291902-(n-Propoxy)ethyl 3-aminocrotonateHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

생성물 1

HCID 1358334242-(n-Propoxy)ethyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate수율 95.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 530 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 450 mg of 3-nitrobenzaldehyde and 560 mg of 2-(n-propoxy)ethyl 3-aminocrotonate in 3 ml of isopropyl alcohol was heated under reflux for 8 hours. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel using benzene-acetonitrile (10:1) as eluent to give 1.35 g of 2-(n-propoxy)ethyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate. Recrystallization from n-hexane-isopropylalcohol afforded pale yellow crystals, m.p. 129°-130° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-cdf59e3109a848d0a79f78a5454db494
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705786

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