Morpholine → Morpholino(3-nitrophenyl)methanone

HRID 2736

반응식

HRID 2736 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O1CCCC1.ClCCl.C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)=[O:9])([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 8083MorpholineHCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 225453Morpholino(3-nitrophenyl)methanone수율 89.8%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

In tetrahydrofuran (100 ml) and dichloromethane (100 ml), 3-nitrobenzoic acid (7.58 g) was dissolved. Then 1-hydroxybenzotriazole (6.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.57 g), and morpholine (9.47 g) were added to the solution. The mixture was stirred at room temperature overnight. After the reaction was completed, chloroform was added to the solution. The mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution, and distilled water. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate) to obtain the above-captioned compound ([13]-(132)-158) (9.62 g) as white crystals.

후처리

  1. washThe mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution
  2. distillationdistilled water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate)

출처 및 근거

ORD 기록
ord-92408f87220947e8aa462aa1b48b9d43
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731310

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