Imidazole → N-[(p-phenoxyphenoxy)-n-propyl]-imidazole

HRID 249360Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[H][H].[O:10]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][CH2:23][CH2:24]Br)=[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][CH2:24][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:26][CH:27]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.98 g of 80% strength sodium hydride is added in portions to a solution of 4.25 g of imidazole in 70 ml of dimethylformamide. Upon completion of hydrogen evolution the mixture is stirred for a further 3 hours at 60° C., after which a solution of 18.42 g of 3-[4-(phenoxy)-phenoxy]-1-bromopropane in 40 ml of dimethylformamide is added. The mixture is heated for 8 hours at 80° C. and then poured into 2.5 liters of ice water. The solid which separates out is filtered off in a desiccator, dried over calcium chloride and purified by filtration over silica gel. There is obtained 14.5 g (82%) of N-[(p-phenoxyphenoxy)-n-propyl]-imidazole; m.p.: 54.5°-55.5° C.

Workup

filtrationThe solid which separates out is filtered off in a desiccator
dry with materialdried over calcium chloride
filtrationpurified by filtration over silica gel

Sources & evidence

ORD record: ord-116358a49449453db4d67acf3cd2820f
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05214064

Reaction notes

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