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

HRID 1078211노트

반응식

HRID 1078211 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 53806442HCID 53806442, 화합물HCID 86749733Potassium (chloro)methanesulfonate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8e6da023a783438181563b276b29f96a
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05547952

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