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Water → 7-benzenesulfonyl-4-(2-dimethylamino-ethyl)-4H-benzo[1,4]oxazin-3-one

HRID 2224062
Notes
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Reaction equation

HRID 2224062 reaction equation
[C:1]1([S:7]([C:10]2[CH:20]=[CH:19][C:13]3[NH:14][C:15](=[O:18])[CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=O)C>[C:1]1([S:7]([C:10]2[CH:20]=[CH:19][C:13]3[N:14]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:15](=[O:18])[CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 586415157-benzenesulfonyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 115450027-benzenesulfonyl-4-(2-dimethylamino-ethyl)-4H-benzo[1,4]oxazin-3-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 7-benzenesulfonyl-4H-benzo[1,4]oxazin-3-one (0.09 g., 0.3 mmol), (2-chloro-ethyl)-dimethyl-amine hydrochloride (0.056 g., 0.39 mmol) and potassium carbonate (0.095 g., 0.69 mmol) in 0.7 mL ethyl acetate was refluxed for 1 hour. To the reaction mixture was added 0.75 mL water, and reflux was continued for 3 hours. 30 mL Ethyl acetate was added, and the reaction mixture was washed three times with 15 mL water, dried over magnesium sulfate and concentrated in vacuo. The residue was purifed by flash chromatography (0 to 5% methanol in dichloromethane) to afford 0.055 g (0.15 mmol, 50%) of 7-benzenesulfonyl-4-(2-dimethylamino-ethyl)-4H-benzo[1,4]oxazin-3-one. MS: 361 (M+H)+, mp: 232.9-235.3° C. (HCl salt).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturereflux
  3. washthe reaction mixture was washed three times with 15 mL water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c48227525044038b5638d9d8f51d87d
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07378415B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes