Aniline → 4-Acetamidobenzenesulfonanilide

HRID 889510

Reaktionsgleichung

Reaktionsgleichung von HRID 889510
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[C:21]1([NH:20][S:9]([C:8]2[CH:13]=[CH:14][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:11])=[O:10])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 8481N-Acetylsulfanilyl chlorideHCID 517045Sodium Acetate

Produkt 1

HCID 7700104-Acetamidobenzenesulfonanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-Acetylsulfanilyl chloride 1 (55 g, 236 mmol) was added in portion to a stirring, 0° C. suspension of sodium acetate (48.4 g, 590 mmol) and aniline 2 (22 mL, 236 mmol) in ethanol (300 mL). The reaction mixture was stirred at room temperature overnight and then poured into ice-cold water (1.5 L) with vigorous stirring. After stirring for 1 h, the white solid that gradually precipitated was collected by filtration. The filter cake was washed with ice-cold water, dried under vacuum, and recrystallized from hot ethanol to give N-[4-[(phenylamino)sulfonyl]phenyl]acetamide (3) (also called 137-19 or LED137) (41 g, 60%) as a white solid, mp 209-210° C. 1H NMR (CD3OD, 400 MHz) δ 7.64 (br s, 4H), 7.18 (t, J=7.6 Hz, 2H), 7.06-7.00 (m, 3H), 2.10 (s, 3H).

Aufarbeitung

  1. stirringAfter stirring for 1 h
  2. customthe white solid that gradually precipitated
  3. filtrationwas collected by filtration
  4. washThe filter cake was washed with ice-cold water
  5. customdried under vacuum
  6. customrecrystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7a322d04849949159a77be1213ea74e3
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252841B2

Verknüpfte Notizen

Wird geladen…