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

HRID 1644388
Notes
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Reaction equation

HRID 1644388 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 61147Bromoacetyl bromideHCID 6432182-Amino-4-(ethylsulphonyl)phenol

Product 1

HCID 27364706-(ethylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes