Water → 2-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamide

HRID 50527

반응식

HRID 50527 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[Li].[S:12]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20]Br)([OH:15])(=[O:14])=[O:13].O>C(O)C>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([S:7]([CH2:20][C:19]([NH:18][CH2:17][CH2:16][S:12]([OH:15])(=[O:14])=[O:13])=[O:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10818p-Toluenesulfinic acidHCID 3028194Lithium4회HCID 19908000N-(2-sulfoethyl)-2-bromoacetamide

생성물 1

HCID 223236362-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamide수율 89%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a 5-liter flask equipped with a mechanical stirrer and reflux condenser was added p-toluenesulfinic acid, lithium salt (308.57 g), N-(2-sulfoethyl)-2-bromoacetamide, lithium salt (527.39 g), water (180 ml), and ethyl alcohol (3380 ml). The resulting suspension was heated to reflux. After about an hour of reflux, nearly all of the reactants had dissolved. Reflux was continued another four hours, and the solution was filtered hot through a Celite pad to remove some haziness. The solution was cooled overnight to room temperature. The solid that formed was collected and washed with 1 liter of 95% ethyl alcohol/water. The white solid was air dried and then dried at high vacuum, providing 553.88 g (89% yield) of 2-(4-methylphenyl)sulfonyl-N-(2-sulfoethyl)acetamide, lithium salt (Intermediate 1). HPLC analysis showed no detectable impurities. Ion chromatography indicated 0.035 weight % bromide and 1.8 weight % lithium. The material exhibited an acceptable proton spectrum.

후처리

  1. customTo a 5-liter flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe resulting suspension was heated to reflux
  4. temperatureAfter about an hour of reflux
  5. dissolutionnearly all of the reactants had dissolved
  6. temperatureReflux
  7. filtrationthe solution was filtered hot through a Celite pad
  8. customto remove some haziness
  9. temperatureThe solution was cooled overnight to room temperature
  10. customThe solid that formed
  11. customwas collected
  12. washwashed with 1 liter of 95% ethyl alcohol/water
  13. customdried
  14. customdried at high vacuum

출처 및 근거

ORD 기록
ord-99b26d7420294a7bb2aec59a2be9cbb0
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713241B2

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