4-Hydrazinobenzenesulfonic acid → 2,3-Dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

HRID 1686154

反応式

HRID 1686154 の反応式
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)N.[CH3:13][CH:14]([C:23](=O)[CH3:24])[CH2:15][CH2:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:21])=[O:20]>C(O)(=O)C>[CH3:24][C:23]1[C:14]([CH3:13])([CH2:15][CH2:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:21])=[O:20])[C:8]2[C:3](=[CH:4][CH:5]=[C:6]([S:9]([OH:12])(=[O:11])=[O:10])[CH:7]=2)[N:1]=1

参加物

4

反応物 2

HCID 668254-Hydrazinobenzenesulfonic acidHCID 579033515-Methyl-6-oxoheptanesulfonic acid

生成物 1

HCID 593662262,3-Dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-Hydrazinobenzenesulphonic acid (7.5 g), 5-methyl-6-oxoheptane-1-sulphonic acid (11.0 g) and acetic acid (50 ml) were heated under reflux under nitrogen for 6 hrs, during which time all of the suspended solid dissolved. The solvent was then evaporated under vacuum and the residue triturated with 2-propanol at 80° C. to give a light brown solid in suspension. The mixture was allowed to cool to ambient temperature, the solid collected by filtration, washed with 2-propanol and diethyl ether and dried under vacuum. The product was purified by HPLC, collecting the major peak detected at 270 nm. (Phenomenex Jupiter 15 μC18 300 A, 250×50 mm. 100 ml/min. 0.5 g per run. Eluant isocratic water+0.1% TFA). Product fractions were pooled and evaporated to give 11.1 g.

後処理

  1. temperatureunder reflux under nitrogen for 6 hrs, during which time all of the suspended solid
  2. dissolutiondissolved
  3. customThe solvent was then evaporated under vacuum
  4. customthe residue triturated with 2-propanol at 80° C.
  5. customto give a light brown solid in suspension
  6. filtrationthe solid collected by filtration
  7. washwashed with 2-propanol and diethyl ether
  8. customdried under vacuum
  9. customThe product was purified by HPLC
  10. customcollecting the major peak
  11. customevaporated
  12. customto give 11.1 g

出典と根拠

ORDレコード
ord-819934ff080e4084b63cf61dbd2f33e7
出典データセット
uspto-grants-2012_04
特許番号
US08148539B2

関連ノート

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