Acetic Anhydride → HCID 10777427, compound

HRID 1896566Notes

Reaction equation

HRID 1896566 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, compoundYield 87.4%

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 (87%) 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-72991a1cdaf7433da793b23737bcd69c
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

Loading…