Ammonium Hydroxide → HCID 21107907, compound

HRID 1765963Notes

Reaction equation

[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[C:12]1([C:18]2[C:26]3[N:25]=[C:24]([CH:27]([OH:29])[CH3:28])[NH:23][C:22]=3[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH4+].[OH-]>OS(O)(=O)=O>[C:12]1([C:18]2[C:26]3[N:25]=[C:24]([C:27](=[O:29])[CH3:28])[NH:23][C:22]=3[C:21]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 1.38 g (4.7 mmol) potassium dichromate in 8.5 ml 40% H2SO4 was added dropwise to a stirred suspension of 1.10 g (3.5 mmol) 1-(4,7-diphenyl-1H-benzimidazol-2-yl)ethanol in 15 ml 5% H2SO4. The slurry was stirred at 90° C. for 10 hours, cooled to room temperature and treated with 7 ml conc. NH4OH. The residue was filtered, washed with water (5×10 ml) and extracted with acetone (10×30 ml). The combined extracts were filtered trough a 0.5 cm layer of silica and the filtrate evaporated. The residue was re-crystallized from ethyl acetate-cyclohexane. Yield—0.57 g (52.1%). 1H NMR (250 MHz, CDCl3), δ, ppm: 2.83 (s, 3H), 7.44–7.64 (m, 10H); 8.14 (d, 7.6 Hz, 2H), 10.22 (br.s).

Workup

temperaturecooled to room temperature
filtrationThe residue was filtered
washwashed with water (5×10 ml)
extractionextracted with acetone (10×30 ml)
filtrationThe combined extracts were filtered trough a 0.5 cm layer of silica
customthe filtrate evaporated
customThe residue was re-crystallized from ethyl acetate-cyclohexane

Sources & evidence

ORD record: ord-3c94635fddc942bcbcfb6cbc5b5e7f63
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229943B2

Reaction notes

Loading…