Ethylene Glycol → N-Benzyl-3,5-dimethylaniline

HRID 1243007노트

반응식

HRID 1243007 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[CH2:9]([NH:16][C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzene

생성물 1

HCID 10176701N-Benzyl-3,5-dimethylaniline수율 84%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 5-iodo-m-xylene (144 μl, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.5) afforded 5-(N-benzyl)amino-m-xylene (177 mg, 84% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144–1157.

출처 및 근거

ORD 기록
ord-cd0a782c6e844affa8e4491609cda759
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115784B2

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