Ammonium Hydroxide → SB203580

HRID 2293494Notes

Reaction equation

HRID 2293494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[NH4+].[OH-:28]>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:26])=[O:28])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 98418634-[4-(4-fluorophenyl)-2-(4-methylsulfanylphenyl)-1H-imidazol-5-yl]pyridine

Product 1

HCID 176155SB203580Yield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 4-(4-fluorophenyl)-2-(4-methylthiophenyl)-5-(4-pyridyl)-1H-imidazole (0.80 g, 2.2 mmol) [See Ex. 17 above] in glacial acetic acid (15 mL) was added a solution of K2S2O8 (0.72 g, 2.6 mmol) in H2O (20 mL.). Additional glacial acetic acid (15 mL,) was added to ensure homogeneity, and the resulting solution was stirred at rt for 18 h. The mixture was then poured into H2O, and the pH was adjusted to neutral by the addition of conc. NH4OH. The solid which formed was collected by filtration to afford the title compound (0.65 g, 78%) as a tan solid, which was recrystallized from MeOH: mp 250°-252° C.

Workup

  1. customThe solid which formed
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5750f6f17706438eb1e19374d67c0287
Source dataset
uspto-grants-1997_11
Patent number
US05686455

Reaction notes

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