Tetrahydrofuran → Morpholino(3-nitrophenyl)methanone

HRID 1261987

反応式

HRID 1261987 の反応式
[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].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O1CCCC1.C(=O)(O)[O-].[Na+]>>[N:13]1([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

参加物

7

反応物 6

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 225453Morpholino(3-nitrophenyl)methanone収率 98.4%

実験手順

m-Nitrobenzoic acid (2.00 g, 0.0120 mol), Morpholine (1.25 g, 0.0144 mol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.29 g, 0.0120 mol) and 1-Hydroxybenzotriazole (0.40 g, 0.0030 mol) were dissolved in Tetrahydrofuran (35 mL, 0.43 mol) and the reaction was allowed to stir overnight at room temperature. The reaction mixture was poured over saturated sodium bicarbonate, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 2.79 g of Morpholin-4-yl-(3-nitro-phenyl)-methanone. (M+H)=237.5.

後処理

  1. extractionorganics were extracted with ethyl acetate/dichloromethane
  2. dry with materialCombined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

出典と根拠

ORDレコード
ord-1ea538fb473f4490b0bd3f1e33c1c298
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

関連ノート

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