P-Anisidine → 1-(2,2-Dimethoxyethyl)-3-(4-methoxyphenyl)-1-(4-phenoxyphenyl)urea

HRID 723339Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].[CH3:22][O:23][CH:24]([O:40][CH3:41])[CH2:25][NH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:28]=1>CN(C)C=O>[CH3:22][O:23][CH:24]([O:40][CH3:41])[CH2:25][N:26]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)[C:10]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-methoxyaniline (1.9 g) in dimethylformamide (3 ml) was added dropwise to a solution of carbonyidiimidazole (2.51 g) in dimethylformamide (15 ml) at 0° C. After a reaction time at 0° C. of 15 minutes, the reaction was allowed to continue at room temperature for 45 minutes. Then (2,2-dimethoxyethyl)-(4-phenoxyphenyl)amine (4.1 g) in dimethylformamide (2 ml) was added, and the mixture was heated at 80° C. for 2 hours. After cooling, volatiles were removed and the residue was taken up in ethyl acetate. The organic phase was washed with water and saturated brine. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 422.49 (C24H26N2O5); MS (ESI): 423 ([M+H]+), was obtained in this way.

Workup

waitto continue at room temperature for 45 minutes
temperatureAfter cooling
customvolatiles were removed
washThe organic phase was washed with water and saturated brine
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customMS (ESI): 423 ([M+H]+), was obtained in this way

Sources & evidence

ORD record: ord-b6949a51fead49749a75d4ec9d09091f
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141561B2

Reaction notes

Loading…