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Potassium Carbonate → 7-benzenesulfonyl-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 2224084
Notes
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Reaction equation

HRID 2224084 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:17][CH2:18][C:19](Br)([CH3:21])[CH3:20])=[C:14]([OH:16])[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:24].[K+].[K+]>CN(C=O)C.Cl>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]3[NH:17][C:18](=[O:24])[C:19]([CH3:21])([CH3:20])[O:16][C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68434859HCID 68434859, compound

Product 1

HCID 586415337-benzenesulfonyl-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The crude 5-benzenesulfonyl-2-(2-bromo-2-methyl-propylamino)-phenol from step 1 was dissolved in 10 mL DMF and potassium carbonate (0.565 g., 4.096 mmol) was added. The reaction mixture was heated to 80° C. with stirring for 2 hours, then cooled to room temperature and poured onto 100 g of ice in 150 mL 10% aqueous hydrogen chloride. The resulting solid was filtered and dried under vacuum for 18 hours to give 0.570 g (1.79 mmol) of 7-benzenesulfonyl-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MS: 316 (M−H)−.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. customdried under vacuum for 18 hours

Sources & evidence

ORD record
ord-edbc13968bd64687bcc4bc43cbcb73fe
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07378415B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes