4-Nitrophenol → 5,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

HRID 72359

反応式

HRID 72359 の反応式
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O-:10])=[O:9].[H-].[Na+].[CH3:20][C:21](=[C:23]([CH3:25])[CH3:24])[CH3:22]>ClCCl.C1COCC1>[CH3:20][C:21]1([CH3:22])[C:23]([CH3:25])([CH3:24])[O:7][C:6]([O:17][C:14]2[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)=[N:5][S:2]1(=[O:4])=[O:3]

参加物

7

反応物 4

HCID 9804-NitrophenolHCID 112502,3-Dimethyl-2-buteneHCID 24758Sodium hydrideHCID 70918Chlorosulfonyl isocyanate

生成物 1

HCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide収率 16.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

7.40 g of chlorosulfonyl isocyanate and 7.27 g of 4-nitrophenol were dissolved in 75 ml of dichloromethane and stirred at room temperature for 90 minutes. The reaction solution was freed of the solvent under reduced pressure, and the residue was dissolved in 50 ml of THF and, under inert gas and at −78° C., admixed with 2.18 g of sodium hydride. After stirring for 5 minutes, 4.38 g of 2,3-dimethyl-2-butene were added and the reaction mixture was heated, gradually because of commencement of evolution of gas, to 35° C. After stirring for 30 minutes, the suspension was added to ice and the resulting THF/water mixture was extracted twice with 100 ml of ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (2.76 g) was thus obtained with a molecular weight of 328.4 g/mol (C13H16N2O6S).

後処理

  1. stirringAfter stirring for 5 minutes
  2. temperaturethe reaction mixture was heated, gradually because of commencement of evolution of gas, to 35° C
  3. stirringAfter stirring for 30 minutes
  4. additionthe suspension was added to ice
  5. extractionthe resulting THF/water mixture was extracted twice with 100 ml of ethyl acetate
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified in a purification laboratory by means of preparative HPLC

出典と根拠

ORDレコード
ord-06644515f77a437daf82552c54c20ebf
出典データセット
uspto-grants-2014_09
特許番号
US08828994B2

関連ノート

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