Sodium hydride → HCID 15258279, compound

HRID 571255Notes

Reaction equation

HRID 571255 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 784192(3H)-Benzoxazolone, 6-nitro-

Product 1

HCID 15258279HCID 15258279, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-nitrobenzo[d]oxazol-2(3H)-one (0.500 g, 2.78 mmol) in DMF (10 ml) was cooled to 0° C. NaH (60% w/w dispersion in mineral oil, 0.133 g, 3.33 mmol) was added, and the reaction was allowed to warm to room temperature and stirred for 15 minutes. The mixture was cooled to 0° C., methyl 2-bromoacetate (0.309 ml, 3.33 mmol) was added, and the reaction was warmed to room temperature and stirred for 4 hours. The mixture was partitioned between ethyl acetate and 1N HCl. The organic phase was washed several times with brine and dried over sodium sulfate. The solvent was removed, and the crude was purified by trituration with diethyl ether (50 ml) affording methyl 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.570 g, 2.260 mmol, 81% yield). MS/ESI+ 252.9 [MH]+.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. temperaturethe reaction was warmed to room temperature
  3. stirringstirred for 4 hours
  4. customThe mixture was partitioned between ethyl acetate and 1N HCl
  5. washThe organic phase was washed several times with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed
  8. customthe crude was purified by trituration with diethyl ether (50 ml)

Sources & evidence

ORD record
ord-3a014a70eec34f80b3d99e6e66d65fec
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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