2-Bromoethanol → HCID 178442866, compound

HRID 1510592Notes

Reaction equation

[CH2:1]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Br:28][CH2:29][CH2:30][OH:31]>C(#N)C>[Br-:28].[OH:31][CH:30]([N+:25]1[CH:26]=[CH:27][N:23]([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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:24]=1)[CH3:29]

Participants

Conditions

Temperature: 90 °C

Procedure

Approximately 3.76 g (0.010 mol) of 1-docosanylimidazole and about 1.45 g (0.012 mol) of 2-bromoethanol were dispersed into 100 mL of acetonitrile. The mixture was refluxed at 90° C. for approximately 24 hours under stirring condition, and subsequently cooled down to room temperature. The precipitate was filtered and washed with ethyl ether. The final product: 1-hydroxyethyl-3-docosanylimidazolium bromide was obtained after being dried in a vacuum oven. The yield was about 90.8% and the melting point was about 76.5° C. The spectra of 1H NMR (DMSO-d6 as the solvent, δ, ppm) was 9.107 (N—CH—N, s, 1H), 7.743 (N—CH—CH, s, 1H), 7.712 (N—CH—CH, s, 1H), 4.192 (N—CH2—CH2—OH, t, 2H), 4.141 (N—CH2—CH2—OH, t, 2H), 3.706 (N—CH2—C21H43, t, 2H), 1.754 (N—CH2—CH2—C20H41, m, 2H), 1.202 (N—CH2—CH2—(CH2)19, m, 38H), 0.822 (CH3, t, 3H).

Workup

temperaturesubsequently cooled down to room temperature
filtrationThe precipitate was filtered
washwashed with ethyl ether

Sources & evidence

ORD record: ord-2b3d2a4989f344f988da5749504bbda1
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211958B2

Reaction notes

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