1-(2-Bromoethyl)-4-methoxybenzene → N'-[4-(4-methoxyphenethyloxy)phenyl]-N-methoxy-N-methylurea

HRID 65822

Reaction equation

[O-]CC.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:18])[N:14]([O:16][CH3:17])[CH3:15])=[CH:8][CH:7]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26]Br)=[CH:23][CH:22]=1>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][O:5][C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:18])[N:14]([O:16][CH3:17])[CH3:15])=[CH:8][CH:7]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a solution of 8.8 g of sodium ethoxide in 200 ml of N,N-dimethylformamide is added 27 g of N'-(4-hydroxyphenyl)-N-methoxy-N-methylurea. To the mixture is added dropwise a solution of 27 g of 4-methoxyphenethyl bromide in 100 ml of N,N-dimethylformamide. The mixture is then gradually heated to 100° C., kept at the same temperature for 5 hours and then poured into ice water. The precipitated crystals are filtered, washed with water, ethanol and ether in this order and air-dried. The product is recrystallized from ethanol to obtain 11.8 g of N'-[4-(4-methoxyphenethyloxy)phenyl]-N-methoxy-N-methylurea as white needles, M.P. 100°-101° C.

Workup

filtrationThe precipitated crystals are filtered
washwashed with water, ethanol and ether in this order
customair-dried
customThe product is recrystallized from ethanol

Sources & evidence

ORD record: ord-148bed485be84463b87cf3e84fc03d56
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04129436

Linked notes

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