Sodium hydride → HCID 11629847, compound

HRID 2067090Notes

Reaction equation

HRID 2067090 reaction equation
[H-].[Na+].[F:3][C:4]1[C:12]2[O:11][C:10](=[O:13])[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.Br[CH2:15][C:16]([NH2:18])=[O:17]>CN(C=O)C>[F:3][C:4]1[C:12]2[O:11][C:10](=[O:13])[N:9]([CH2:15][C:16]([NH2:18])=[O:17])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 21989976HCID 21989976, compound

Product 1

HCID 11629847HCID 11629847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, NaH (in oil, 60 w/w, 1.8 g, 45.15 mmol) is carefully added by portion into a solution of 7-fluoro-1,3-benzoxazol-2(3H)-one 2 (5.76 g, 37.62 mmol) in dried DMF (80 ml) at 0° C. After 0.25 h, 2-bromo-acetamide (6.22 g, 45.15 mmol) is added. The reaction mixture is stirred for 1 h at room temperature, quenched with water, concentrated in vacuo and the residue is recrystallized in EtOH/H2O (80/20 (v/v)) to afford 2-(7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide.

Workup

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. customthe residue is recrystallized in EtOH/H2O (80/20 (v/v))

Sources & evidence

ORD record
ord-f62a90a0c3424176b0b988b78348dbd4
Source dataset
uspto-grants-2012_10
Patent number
US08293775B2

Reaction notes

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