Water → 6-Chloro-2-hydroxy-3-nitrobenzenesulfonamide

HRID 396277노트

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HRID 396277 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[H-].[Na+].[OH2:18]>C(OCC)(=O)C>[Cl:11][C:4]1[C:3]([S:12]([NH2:15])(=[O:14])=[O:13])=[C:2]([OH:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 962Water2회HCID 24758Sodium hydrideHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

생성물 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamide수율 77%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
45 °C

실험 절차

A mixture of 2,6-dichloro-3-nitrobenzenesulfonamide (2.61 g, 9.64 mmol), 60% sodium hydride (1.15 g, 28.9 mmol) and water (174 μL, 9.64 mmol) was heated to 45° C. while kept at argon atmosphere for 3 days. The reaction was monitored by 1H NMR. 0.1 equivalent water was added to the mixture when the reaction was not completed. The solvent was evaporated when the reaction almost completed indicated by 1H NMR. The residue was diluted with ethyl acetate and washed with 1N aq. HCl. The solvent was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v), gave the desired product (1.87 g, 77%). EI-MS (m/z)250.84, 252.89 (M−).

후처리

  1. additionwas added to the mixture when the reaction
  2. customThe solvent was evaporated when
  3. customthe reaction
  4. washwashed with 1N aq. HCl
  5. concentrationThe solvent was concentrated
  6. customto give the crude material
  7. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/48/2, v/v/v)

출처 및 근거

ORD 기록
ord-aa8dcc0cb7e14153906f92d8bb186c5d
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608077B2

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