Cesium carbonate → 6-(Ethylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1644388Notes

Reaction equation

[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([NH2:13])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][C:22](Br)=[O:23]>CN(C=O)C>[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH2:21][C:22](=[O:23])[NH:13][C:8]=2[CH:7]=1)(=[O:5])=[O:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%).

Workup

customAfter aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane

Sources & evidence

ORD record: ord-06932f5287e946bf9c068a378e150893
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124602B2

Reaction notes

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