Water → HCID 18316650, compound

HRID 275796Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:12]2[NH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9][C:8]=2[C:7]([O:17][CH3:18])=[CH:6][CH:5]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.O>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:3][C:4]1[C:12]2[N:11]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[C:10]([C:13]([F:14])([F:15])[F:16])=[N:9][C:8]=2[C:7]([O:17][CH3:18])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium hydride (0.16 g; 60% dispersion in oil) was added to a solution of 4-bromo-7-methoxy-2-trifluoromethylbenzimidazole (1.0 g) in N,N-dimethylformamide (20 ml). The mixture was stirred at room temperature for 10 minutes before addition of 4-methoxybenzyl chloride (0.56 ml) and catalytic tetrabutylammonium iodide. The reaction was heated at 90° C. for 6 h, then poured into water (100 ml) and extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with water (100 ml) and brine (50 ml), dried over magnesium sulphate, evaporated in vacuo and purified by flash chromatography eluting with 33% ethyl acetate in hexane to afford the title compound as a white solid (0.52 g).

Workup

extractionextracted with ethyl acetate (2×100 ml)
washThe combined organic phases were washed with water (100 ml) and brine (50 ml)
dry with materialdried over magnesium sulphate
customevaporated in vacuo
custompurified by flash chromatography
washeluting with 33% ethyl acetate in hexane

Sources & evidence

ORD record: ord-4d63fe54143147838040276999e60fed
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353010B1

Reaction notes

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