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

HRID 2224055
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HRID 2224055 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-d0b79a38c5e04ce1bf0e5fc1e5abe20d
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378415B2

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