Bis(2-bromoethyl) ether → HCID 71599638, compound

HRID 1622443Notes

Reaction equation

[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:20])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=3[CH3:19])[C:6]=2[CH:5]=[C:4]([NH2:21])[CH:3]=1.Br[CH2:23][CH2:24][O:25][CH2:26][CH2:27]Br.CCN(C(C)C)C(C)C>C(O)CO.O>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:20])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=3[CH3:19])[C:6]=2[CH:5]=[C:4]([N:21]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-bromo-3-(3-chloro-2-methylbenzyl)-2-methyl-3H-benzo[d]imidazol-5-amine (85 g, 233 mmol), 1-bromo-2-(2-bromoethoxy)ethane (108 g, 466 mmol) and DIPEA (60 g, 466 mmol) in ethylene glycol (1 L) was stirred at 100° C. for 18 h. It was cooled to rt, and diluted with water (1 L) and extracted with DCM (500 mL×4). The combined organic layers were washed with brine, dried over sodium sulphate and evaporated. The residue was purified by column chromatography (eluted with petroleum ether/ethyl acetate=1/1) to give the product (48 g, 47.5%) as a yellow solid; LC/MS: MS (ES+) m/e 434 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 2.46 (s, 3H), 3.04-3.07 (m, 4H), 3.68-3.72 (m, 4H), 5.47 (s, 2H), 6.04 (d, J=8.1 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H), 7.06 (t, J=8.1 Hz, 1H), 7.09 (d, J=2.1 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H).

Workup

temperatureIt was cooled to rt
extractionextracted with DCM (500 mL×4)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulphate
customevaporated
customThe residue was purified by column chromatography (eluted with petroleum ether/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-c12f775a587a47c5bbc28637debed296
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778937B2

Reaction notes

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