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

HRID 986902

反応式

HRID 986902 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 10818p-Toluenesulfinic acidHCID 3028194Lithium4 回HCID 19908000N-(2-sulfoethyl)-2-bromoacetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0a91b67beb24a7f926ab7e0a2e24c7b
出典データセット
uspto-grants-2003_10
特許番号
US06630291B1

関連ノート

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