Sodium hydride → N-[(p-phenoxyphenoxy)-ethyl]-4,5-dichloroimidazole

HRID 2166097Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[H-].[Na+].[O:10]([C:17]1[CH:36]=[CH:35][C:20]([O:21][CH2:22][CH2:23]C2C=C(S([O-])(=O)=O)C=CC=2C)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C)C=O>[O:10]([C:17]1[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH2:23][N:3]2[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]2)=[CH:35][CH:36]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 8.43 g of 4,5-dichloroimidazole, 80 ml of dimethylformamide and 1.83 g of sodium hydride is heated, with stirring, for 3 hours at 60° C. Subsequently, a solution of 23.04 g of 2-[(p-phenoxyphenoxy)-ethyl]p-toluenesulfonate in 40 ml of dimethylformamide is dripped in. The mixture is heated for 12 hours at 100° C., cooled, poured into 50 ml of ice water, and extracted several times with ethyl acetate, and the combined extracts are washed first with 5% strength aqueous sodium hydroxide solution and then with water. Drying over sodium sulfate, removal of the solvent under reduced pressure and recrystallization from methyl tert-butyl ether gives 16.9 g (81%) of N-[(p-phenoxyphenoxy)-ethyl]-4,5-dichloroimidazole; m.p.: 89°-91° C.

Workup

temperatureis heated
temperatureThe mixture is heated for 12 hours at 100° C.
temperaturecooled
extractionextracted several times with ethyl acetate
washthe combined extracts are washed first with 5% strength aqueous sodium hydroxide solution
dry with materialDrying over sodium sulfate, removal of the solvent under reduced pressure and recrystallization from methyl tert-butyl ether

Sources & evidence

ORD record: ord-819b87d2270043109f26c879fdff0269
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04943585

Reaction notes

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