Chloroacetyl chloride → HCID 22312860, compound

HRID 2224060Notes

Reaction equation

HRID 2224060 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[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(C(C)=O)C.CCOC(C)=O>[C:11]1([S:8]([C:6]2[CH:5]=[CH:4][C:3]3[O:17][CH2:24][C:25](=[O:26])[NH:1][C:2]=3[CH:7]=2)(=[O:10])=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 133660362-Amino-4-phenylsulfonylphenol

Product 1

HCID 22312860HCID 22312860, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-benzenesulfonyl-phenol (2.064 g, 8.2 mmol) was dissolved in 15 mL of methyl ethyl ketone, and NaHCO3 (1.39 g, 9.1 mmol) was added to this solution. The reaction mixture was cooled to 0° C., and 2-chloroacetyl chloride (0.215 mL, 9.0 mmol) was added dropwise while stirring. The reaction mixture was stirred for 2 hours, after which K2CO3 (1.37 g, 9.95 mmol) was added, and the reaction was brought to reflux for three hours. The reaction mixture was cooled and 150 mL of EtOAc was added. The organic layer was washed three times with 50 ml water, once with 50 mL saturated brine, dried (Na2SO4) and concentrated in vacuo to yield a crude solid, which was purified by flash chromatography (10-30% EtOAc in hexanes), to afford 6-benzenesulfonyl-4H-benzo[1,4]oxazin-3-one (2.176 g, 7.52 mmol, 92%). MS: 290 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. temperatureto reflux for three hours
  3. temperatureThe reaction mixture was cooled
  4. washThe organic layer was washed three times with 50 ml water
  5. dry with materialonce with 50 mL saturated brine, dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a crude solid, which
  8. customwas purified by flash chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7164fdef660641b1b6783a38f50cf315
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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