1-Benzylimidazole → N1-benzyl-N3-[3-(7-chlorodibenzofuran-3-yloxy)-propyl]-imidazolium bromide

HRID 615178Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=3[O:11][C:10]=2[CH:19]=1.[CH2:20]([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1.C(#N)C>[Br-:1].[CH2:20]([N+:27]1[CH:31]=[CH:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]4[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=4[O:11][C:10]=3[CH:19]=2)[CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of 14 g (0.041 mole) of 1-bromo-3-(7-chlorodibenzofuran-3-yloxy)-propane and 7.9 g (0.05 mole) of N-benzylimidazole in 25 ml of dry dioxane and 25 ml of dry acetonitrile was stirred for 40 hours at 70° C. The mixture was cooled to 15° C. in an ice bath, and the crystalline precipitate formed was then filtered off under suction, washed with 30 ml of ether and finally with 50 ml of n-pentane, and dried. 15 g (73.2% of theory) of N1 -benzyl-N3 -[3-(7-chlorodibenzofuran-3-yloxy)-propyl]-imidazolium bromide of melting point 162°-166° C. were obtained.

Workup

customthe crystalline precipitate formed
filtrationwas then filtered off under suction
washwashed with 30 ml of ether and finally with 50 ml of n-pentane
customdried

Sources & evidence

ORD record: ord-bacedb950bff4a748a225e827ebef55c
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04497819

Reaction notes

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