1H-Imidazole, 1-tetradecyl- → HCID 178443154, compound

HRID 1943311Notes

Reaction equation

[CH2:1]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Br:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:31][N:32]=2)=[CH:24][CH:23]=1>C1COCC1>[Br-:20].[C:33]1([C:30]2[O:29][C:28]([C:25]3[CH:24]=[CH:23][C:22]([CH2:21][N:17]4[CH:18]=[CH:19][N+:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:16]4)=[CH:27][CH:26]=3)=[N:32][CH:31]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a round-bottomed flask previously purged with anhydrous argon are added 1-tetradecylimidazole [2-5] (1.023 g, 3.9 mmol), 2-(4-bromomethyl-phenyI)-5-phenyl-oxazole (1.215 g, 3.9 mmol) and anhydrous THF (15 mL). The reaction mixture is stirred at 80° C. for 12 hours. The solvent is removed in vacuo and the product is washed with 3 times 10 mL Et2O and dried under reduced pressure at ambient temperature. The product is purified by flash chromatography (silica gel column, elution with DCM-MeOH, MeOH 1% to 7%) and characterized as being an imidazolium salt.

Workup

customTo a round-bottomed flask previously purged with anhydrous argon
customThe solvent is removed in vacuo
washthe product is washed with 3 times 10 mL Et2O
customdried under reduced pressure at ambient temperature
customThe product is purified by flash chromatography (silica gel column, elution with DCM-MeOH, MeOH 1% to 7%)

Sources & evidence

ORD record: ord-b6cc2a8162c74122ae56edcaf7ff3a63
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389940B2

Reaction notes

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