4-Benzyloxyaniline → 3-(4-Benzyloxyphenyl)-1-(2,2-dimethoxyethyl)-1-(4-phenoxyphenyl)urea

HRID 723334Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17].[CH3:28][O:29][CH:30]([O:46][CH3:47])[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:16](=[O:17])[N:32]([CH2:31][CH:30]([O:46][CH3:47])[O:29][CH3:28])[C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:35][CH:34]=2)=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-benzyloxyaniline (199 mg) in dimethylformamide (1 ml) was added dropwise to a solution of carbonyldiimidazole (162 mg) in dimethylformamide (1 ml) at 0° C. After a reaction time at 0° C. of 10 minutes, the reaction was allowed to continue at room temperature for 20 minutes. Then (2,2-dimethoxyethyl)-(4-phenoxyphenyl)amine (273 mg) was added, and the mixture was heated at 80° C. for 1.5 hours. Cooling was followed by dilution with water and extraction with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 498.58 (C30H30N2O5); MS (ESI): 499 ([M+H]+), was obtained in this way.

Workup

waitto continue at room temperature for 20 minutes
temperatureCooling
extractionwas followed by dilution with water and extraction with ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customMS (ESI): 499 ([M+H]+), was obtained in this way

Sources & evidence

ORD record: ord-0f11f72f476a4292a628fef156f83830
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141561B2

Reaction notes

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