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

HRID 255269
Notes
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Reaction equation

HRID 255269 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-ab440ac8d22c4fe5b2350fe463e9cdb3
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07875715B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes