Sodium Iodide → HCID 23081404, compound

HRID 856349Notes

Reaction equation

HRID 856349 reaction equation
CS(O[CH2:6][C:7]1([CH3:18])[O:11][C:10]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]2[CH2:8]1)(=O)=O.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29](=[O:31])[NH:28][N:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C=O)C>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[O:30][C:29](=[O:31])[N:28]([CH2:6][C:7]3([CH3:18])[O:11][C:10]4=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]4[CH2:8]3)[N:27]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 164840335-(4-Bromophenyl)-1,3,4-oxadiazol-2(3H)-oneHCID 23081519HCID 23081519, compound

Product 1

HCID 23081404HCID 23081404, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl methanesulfonate prepared in Example 41 (1.02 g, 3.67 mmol), 5-(4-bromophenyl)-3H-[1,3,4]oxadiazol-2-one (680 mg, 2.82 mmol), potassium carbonate (580 mg, 4.2 mmol), sodium iodide (890 mg, 5.94 mmol) and DMF (15 ml) was stirred at 100° C. for 3 hours. The reaction mixture was allowed to return to room temperature. To the solution, water was added, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water three times, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford 5-(4-bromophenyl)-3-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-3H-[1,3,4]oxadiazol-2-one (17.4 mg, yield 2%) as a light yellow powder.

Workup

  1. customto return to room temperature
  2. extractionthe resulting solution was extracted with ethyl acetate twice
  3. washwashed with water three times
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-9eea6ef427b8490390490fceb2788279
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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