Acetic Anhydride → HCID 10777427, compound

HRID 2178217Notes

Reaction equation

HRID 2178217 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[O:6][CH2:7][C:8](=O)[NH:9][C:4]=2[CH:3]=1.[CH3:13][C:14](OC(C)=O)=[O:15]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[O:6][CH2:7][CH2:8][N:9]([C:14](=[O:15])[CH3:13])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 10777427HCID 10777427, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (7A) (2.5 g, 11.7 mmol) was taken up in DCM (100 mL) and treated with TEA (4.07 mL, 29.2 mmol) followed by Ac2O (2.75 mL, 29.2 mmol). 4-DMAP (0.285 g, 2.34 mmol) was added and the reaction mixture was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a gradient of 0 to 50% EtOAc in hexanes to provide 2.62 g 187%) of the desired compound 1-(6-bromo-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone (7B).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by column chromatography on silica gel eluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-d4542ec8252c4fdb8e5973d6c6abcef1
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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