Sodium Bicarbonate → Methyl 4-acetylamino-5-bromo-3-iodosalicylate

HRID 17538

反応式

HRID 17538 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[I:17](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[C:1]([NH:4][C:5]1[C:6]([I:17])=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 56924451Trimethylbenzylammonium DichloroiodateHCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoate

生成物 1

HCID 86097515Methyl 4-acetylamino-5-bromo-3-iodosalicylate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 4-acetylamino-5-bromosalicylate (I-249) (576 mg, 2.0 mmol) was dissolved in a mixed liquid of methylene chloride (20 ml) and methanol (10 ml), then benzyltrimethylammonium dichloroiodate (835 mg, 2.4 mmol) and sodium bicarbonate (1.1 g, 13.0 mmol) were added, followed by stirring at room temperature for 30 hours. The reaction liquid was filtered, the filtrate was concentrated under reduced pressure, then saturated ammonium chloride water was added to the residue, followed by extraction twice with chloroform, then the organic layer was washed with saturated sodium thiosulfate water, and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid.

後処理

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionsaturated ammonium chloride water was added to the residue
  5. extractionfollowed by extraction twice with chloroform
  6. washthe organic layer was washed with saturated sodium thiosulfate water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration and concentration under reduced pressure
  9. customthe eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid

出典と根拠

ORDレコード
ord-9e819f94cbef4ecca05582838049e421
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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