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

HRID 396277ノート

反応式

HRID 396277 の反応式
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

参加物

5

反応物 3

HCID 962Water2 回HCID 24758Sodium hydrideHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

生成物 1

HCID 112768176-Chloro-2-hydroxy-3-nitrobenzenesulfonamide収率 77%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

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−).

後処理

  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)

出典と根拠

ORDレコード
ord-aa8dcc0cb7e14153906f92d8bb186c5d
出典データセット
uspto-grants-2003_08
特許番号
US06608077B2

反応ノート

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