Nitrogen → 1-(2-((2-Methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene
Reaction equation
N#N.[N+:3]([C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=1)([O-:5])=[O:4].CCN(C(C)C)C(C)C.[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30]Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.O.C(OCC)(=O)C.CCCCCC>[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30][O:13][CH2:12][CH2:11][O:10][C:9]1[CH:14]=[CH:15][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Into a 100 mL 3-neck RBF, equipped with N2 Bubbler and thermo pocket 2-(4-nitrophenoxy)ethanol (10.8 g) in DCM (30 mL), and DIPEA (11.44 g) were added; the reaction mixture was cooled to 0° C. Methoxyethoxymethyl chloride (11.02 g in 20 mL DCM) was added drop wise during 10 min, and the reaction mixture was stirred at room temperature for 16 hr. The reaction was monitored on TLC using ethyl acetate:hexane (5:5) as mobile phase. After completion of the reaction, reaction mixture was poured into water and neutralized with saturated NaHCO3 solution. Product was extracted into DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. to give 10.54 g of 1-(2-((2-methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene.
Workup
- customAfter completion of the reaction, reaction mixture
- extractionProduct was extracted into DCM
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated completely
- customat 40° C.
Sources & evidence
- ORD record
- ord-112ef8de70a54979bf67a9546c649335
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09415049B2
Reaction notes
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