Hydrochloric Acid → 2-(3,5-Di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-4-sulfomethyl-2H-1,4-benzothiazine

HRID 1078211ノート

反応式

HRID 1078211 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[CH:10]=[C:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)([CH3:6])([CH3:5])[CH3:4].Cl[CH2:31][S:32]([O-:35])(=[O:34])=[O:33].[K+].Cl>CC(C)=O>[C:3]([C:7]1[CH:8]=[C:9]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[CH:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:31][S:32]([OH:35])(=[O:34])=[O:33])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)([CH3:6])([CH3:5])[CH3:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 53806442HCID 53806442、化合物HCID 86749733Potassium (chloro)methanesulfonate

生成物 1

HCID 570864732-(3,5-Di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-4-sulfomethyl-2H-1,4-benzothiazine

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a suspension of sodium hydride (60% suspension in paraffin liquid, 0.042 g) in dimethylformaldehyde (1 ml), 2-(3, 5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (0.20 g) dissolved in dimethylformalhyde (2 ml) was added, dropwise, under ice-cooling and a nitrogen atmosphere. The mixture was stirred for 40 minutes at room temperature. To the mixture, potassium (chloro)methanesulfonate (0,096 g) dissolved in dimethylformaldehyde (2 ml) was added, dropwise, and the mixture was stirred for one day at room temperature. 1N hydrochloric acid was added to the mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give the titled compound.

後処理

  1. dissolutiondissolved in dimethylformalhyde (2 ml)
  2. additionwas added
  3. temperaturedropwise, under ice-cooling
  4. additionwas added
  5. stirringdropwise, and the mixture was stirred for one day at room temperature
  6. extractionthe whole was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8e6da023a783438181563b276b29f96a
出典データセット
uspto-grants-1996_08
特許番号
US05547952

反応ノート

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