Ethane, 1-(2-chloroethoxy)-2-methoxy- → 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-nitrobenzene

HRID 1883773Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl>CN(C)C=O>[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)[CH3:1]

Participants

Conditions

Temperature: 100 °C

Procedure

5.0 g of 4-methylaminomethyl-nitrobenzene are dissolved in 30 ml of dimethylformamide and 4.6 g of 2-(2-methoxy-ethoxy)-ethyl chloride are added. After six hours' stirring at 100° C. the solvent is removed and the residue is taken up in ethyl acetate. The organic phase is washed with water and dried over sodium sulphate. After the elimination of the solvent the residue is purified over an aluminium oxide column (activity 2-3) with toluene/ethyl acetate 5:1 as eluant.

Workup

customis removed
washThe organic phase is washed with water
dry with materialdried over sodium sulphate
customAfter the elimination of the solvent the residue is purified over an aluminium oxide column (activity 2-3) with toluene/ethyl acetate 5:1 as eluant

Sources & evidence

ORD record: ord-37ccfe44e36b4529b09f6d9616bcedca
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762180B1

Reaction notes

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