Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 57639715, compound

HRID 2111783Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:33][CH2:34][Cl:35])(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)C>[Cl:35][CH2:34][CH2:33][O:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(3-Hydroxyphenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (5.0 g, 14.5 mmol), tetrabutylammonium iodide (536 mg, 1.5 mmol) and sodium hydroxide (9.8 g, 41.7 mmol) were dissolved in anhydrous ethanol and heated to reflux for 15 min. 2-Chloroethyl tosylate (581 mg, 41.67 mmol, 7.6 mL) was then added and the mixture allowed to stir at 80° C. for 18 h. After this time, the reaction mixture was concentrated in vacuo and the crude product purified by chromatography over silica gel eluting with 50% ethyl acetate/hexanes to 10% methanol in ethyl acetate to give 1-[3-(2-chloroethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide.

Workup

temperatureheated
temperatureto reflux for 15 min
concentrationAfter this time, the reaction mixture was concentrated in vacuo
customthe crude product purified by chromatography over silica gel eluting with 50% ethyl acetate/hexanes to 10% methanol in ethyl acetate

Sources & evidence

ORD record: ord-8b826630abed4da9978e7cb688a33638
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521448B2

Reaction notes

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