Barium hydroxide, octahydrate → Mesityl-2-methyl-4-nitro-1H-imidazole

HRID 584800Notes

Reaction equation

HRID 584800 reaction equation
Br[C:2]1[NH:6][C:5]([CH3:7])=[N:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[N:6]1[CH:2]=[C:3]([N+:8]([O-:10])=[O:9])[N:4]=[C:5]1[CH3:7]

Participants

7

Reactant 3

HCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acidHCID 178433401HCID 178433401, compound

Product 1

HCID 22341351Mesityl-2-methyl-4-nitro-1H-imidazoleYield 70.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 107951,1-DimethoxyethaneSolvent

Procedure

A solution of 5-bromo-2-methyl-4-nitroimidazole (5.0 g, 24 mmol), mesitylboric acid (3.96 g, 24 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol) and barium hydroxide octahydrate (19.1 g, 61 mmol) in 2,2-dimethoxyethane (150 mL) and water (25 mL) was heated at reflux for four hours. After filtered through Celite, the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crystals were washed with ethyl acetate, to give the title compound (4.17 g) as white crystals.

Workup

  1. temperatureat reflux for four hours
  2. filtrationAfter filtered through Celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. washThe resulting crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-354c035aa5624c95b1c77b634412731d
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

Loading…