Sodium hydride → 4-(3-bromo-5-chloro-benzyl)-7-methoxy-4H-benzo[1,4]oxazin-3-one

HRID 1453647Notes

Reaction equation

HRID 1453647 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[NH:7][C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1.[H-].[Na+].[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH2:20]Br>CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH2:20][N:7]1[C:6]2[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:10][CH2:9][C:8]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 116007707-Methoxy-2H-1,4-benzoxazin-3(4H)-oneHCID 223242641-Bromo-3-(bromomethyl)-5-chlorobenzene

Product 1

HCID 223242624-(3-bromo-5-chloro-benzyl)-7-methoxy-4H-benzo[1,4]oxazin-3-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 grams of 7-methoxy-1,4-benzoxazin-3-one (2.8 mmole) was dissolved in 10 ml of dimethylformamide and cooled in an ice bath. 0.17 grams (3.5 mmole) of sodium hydride (60% wt. inn oil) was added, and after 5 minutes 0.8 grams (2.9 mmole) of 3-bromo-5-chloro-benzylbromide was added all at once. The mixture was stirred at ice bath temperature for 1 hour, and then quenched by addition of 1% hydrochloric acid. The product was extracted with ethyl acetate, that was evaporated under reduced pressure to give an oil which was chromatographed via medium pressure eluting with 10% ethyl acetate in hexanes to yield 0.9 grams of 4-(3-bromo-5-chloro-benzyl)-7-methoxy-4H-benzo[1,4]oxazin-3-one as a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. customquenched by addition of 1% hydrochloric acid
  3. extractionThe product was extracted with ethyl acetate, that
  4. customwas evaporated under reduced pressure
  5. customto give an oil which
  6. customwas chromatographed via medium pressure
  7. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8e3aa0201b6a493f8bd5f2fb7396e047
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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