Dimethylformamide → HCID 23081087, compound

HRID 856176Notes

Reaction equation

HRID 856176 reaction equation
[H-].[Na+].[SH:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.CN(C=O)C.CS(O[CH2:23][C:24]1([CH3:35])[O:28][C:27]2=[N:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][N:26]2[CH2:25]1)(=O)=O>O>[CH3:23][C:24]1([CH2:35][S:3][C:4]2[O:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[N:8]=2)[O:28][C:27]2=[N:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][N:26]2[CH2:25]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 23081519HCID 23081519, compoundHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 23081087HCID 23081087, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (50 mg, 1.25 mmol) was added to a mixture of 2-mercaptobenzoxazole (200 mg, 1.3 mmol) and DMF (3 ml) followed by stirring at room temperature for 1 hour. To the reaction mixture, 2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl methanesulfonate prepared in Example 41 (330 mg, 1.2 mmol) was added, and the resulting mixture was stirred at 60-70° C. for 5 hours. The reaction mixture was allowed to return to room temperature. Water was added to the solution, and the resulting mixture was extracted with ethyl acetate twice. The organic phases were combined, washed with 5% sodium hydroxyde solution and water three times, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography(n-hexane/ethyl acetate=1/1) to afford 2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethylthio)benzoxazole (37 mg, yield 9%) as a white powder.

Workup

  1. stirringthe resulting mixture was stirred at 60-70° C. for 5 hours
  2. customto return to room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate twice
  4. washwashed with 5% sodium hydroxyde solution and water three times
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography(n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ebeb3b2339b14389b9c69dbf24b19619
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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