Chloroacetyl chloride → 7-benzenesulfonyl-4H-benzo[1,4]oxazin-3-one

HRID 2224055Notes

Reaction equation

HRID 2224055 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[OH:17].C(=O)(O)[O-].[Na+].Cl[CH2:24][C:25](Cl)=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.CCOC(C)=O>[C:11]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:25](=[O:26])[CH2:24][O:17][C:3]=3[CH:4]=2)(=[O:10])=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 14053206HCID 14053206, compound

Product 1

HCID 586415157-benzenesulfonyl-4H-benzo[1,4]oxazin-3-oneYield 84.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-amino-5-benzenesulfonyl-phenol (0.392 g., 1.57 mmol) in 10 mL of acetonitrile was cooled to O° C. To this solution was added sodium bicarbonate (0.263 g., 3.14 mmol) in 4 mL water. With stirring, 2-chloroacetyl chloride (0.162 mL, 2.097 mmol) was added dropwise over 2 minutes. Stirring was continued for one hour as the reaction mix was warmed to room temperature. Potassium carbonate (0.261 g., 1.89 mmol) was then added and the system was warmed to reflux (85° C.) for two hours. The reaction mixture was added to 50 mL EtOAc, the aqueous fraction was separated and the organic layer was washed twice with 50 mL water, dried over Na2SO4 and concentrated in vacuo. The crude solid was recrystallized from a mixture of 30 mL each of ethanol and water to give 0.382 g (1.32 mmol, 84%) of 7-benzenesulfonyl-4H-benzo[1,4]oxazin-3-one as a yellow solid. MS: 288 (M−H)−. Step 6:

Workup

  1. stirringStirring
  2. additionmix
  3. temperaturethe system was warmed
  4. temperatureto reflux (85° C.) for two hours
  5. customthe aqueous fraction was separated
  6. washthe organic layer was washed twice with 50 mL water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude solid was recrystallized from a mixture of 30 mL each of ethanol and water

Sources & evidence

ORD record
ord-d0b79a38c5e04ce1bf0e5fc1e5abe20d
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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