HCID 18956338, compound → HCID 18956343, compound

HRID 2379896Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][C:24]3[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=3)[C:27](OCC)=[O:28])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][C:24]3[CH:34]=[CH:33][CH:32]=[C:26]([CH2:27][OH:28])[CH:25]=3)[NH:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Part B. A solution of the ester prepared in Part A above (6.57 g, 13.8 mmol) in tetrahydrofuran (20 mL) was added to an ice-cooled slurry of lithium aluminum hydride (1.16 g, 30.5 mmol) in tetrahydrofuran (20 mL). The mixture was warmed to mild reflux for 18 hours, then re-cooled to 0° C. and quenched by the careful sequential addition of water (2 mL), 15% aqueous sodium hydroxide (6 mL), and water (6 mL). The resulting mixture was filtered through celite, dried over anhydrous potassium carbonate, filtered and evaporated to afford the product, 4,5-bis(4-methoxyphenyl)-2-[3-(hydroxymethyl)benzyl]thio-1-H-imidazole, as an oil (5.97 g, 13.8 mmol, 100%). 1H NMR (CDCl3): 7.41-7.07 (8H, m); 6.81 (4H, d, J=8.8 Hz); 4.56 (2H, s); 4.15 (2H, s); 3.79 (6H, s).

Workup

temperatureThe mixture was warmed
temperatureto mild reflux for 18 hours
customquenched by the careful sequential addition of water (2 mL), 15% aqueous sodium hydroxide (6 mL), and water (6 mL)
filtrationThe resulting mixture was filtered through celite
dry with materialdried over anhydrous potassium carbonate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2c2d02751d8c4cef94859877ee0ca84b
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364875

Reaction notes

Loading…