Lithium Hydroxide → 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetic acid

HRID 216602Notes

Reaction equation

HRID 216602 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][CH2:22][C:23]([O:25]CC)=[O:24])=[N:6][CH:5]=1>C1COCC1.C(O)C.O>[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][CH2:22][C:23]([OH:25])=[O:24])=[N:6][CH:5]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59225908ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate

Product 1

HCID 461788622-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetic acidYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide solution (1M, 44 mL, 44.00 mmol) was added to a solution of ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate (9.14 g, 21.96 mmol) in THF (60 mL), ethanol (24 mL) and water (20 mL), and stirred for 4 h. After concentrating, the residue was acidified with aqueous HCl solution (1N, 50 mL), diluted with water (100 mL) and filtered to afford 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetic acid as an off-white solid (8.52 g, 100%).

Workup

  1. concentrationAfter concentrating
  2. additiondiluted with water (100 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-5724855c598843ffbf9518de99416e84
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

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