Hydrochloric Acid → HCID 18426860, compound

HRID 1281137Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:15]=[C:16]([C:19]2[NH:20][C:21]3[CH:27]=[C:26]([Cl:28])[C:25]([Cl:29])=[CH:24][C:22]=3[N:23]=2)[S:17][CH:18]=1.CN(C)[CH:32]=[O:33].Cl>O1CCCC1.O>[Br:13][C:14]1[CH:15]=[C:16]([C:19]2[NH:23][C:22]3[CH:24]=[C:25]([Cl:29])[C:26]([Cl:28])=[CH:27][C:21]=3[N:20]=2)[S:17][C:18]=1[CH:32]=[O:33]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of diisopropylamine (0.67 mL, 4.8 mmol) in tetrahydrofuran (6 mL) was added n-butyllithium (1.6 mol/L in hexanes; 2.7 mL, 4.3 mmol) at 0° C. under nitrogen atmosphere, and the reaction mixture was cooled to −78° C. 2-(4-Bromothiophen-2-yl)-5,6-dichlorobenzimidazole (500 mg, 1.44 mmol) in tetrahydrofuran (14 mL) was added dropwise followed by the addition of dimethylformamide (0.33 mL, 4.3 mmol), and the mixture was stirred for 30 min. Water and hydrochloric acid (1 mol/L) were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was triturated with ethyl acetate to afford 2-(3-bromo-2-formylthiophen-5-yl)-5,6-dichlorobenzimidazole (296 mg, 55%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried on anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-d5976e58ee7a46bdbb10f493365baa60
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06452014B1

Reaction notes

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