1,4-氧氮六环 → Morpholino(3-nitrophenyl)methanone

HRID 2736

反应方程式

HRID 2736 反应方程式
[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]

参与物

8

反应物 4

HCID 80831,4-氧氮六环HCID 8497Nitrobenzoic AcidHCID 757711-羟基苯并三唑(HOBT)HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐

产物 1

HCID 225453Morpholino(3-nitrophenyl)methanone收率 89.8%

试剂、催化剂与溶剂 3

HCID 6212三氯甲烷溶剂HCID 6344二氯甲烷溶剂HCID 8028四氢呋喃溶剂

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-92408f87220947e8aa462aa1b48b9d43
来源数据集
uspto-grants-1998_03
专利号
US05731310

关联笔记

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