2-Phenylacetophenone → 4-(2-Oxo-2-phenylethyl)benzene-1-sulfonamide

HRID 343074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343074
Cl[S:2]([OH:5])(=O)=[O:3].[C:6]1([C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH4+:21].[OH-]>CC(C)=O>[NH2:21][S:2]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:13])=[CH:20][CH:19]=1)(=[O:5])=[O:3]

Komponenten

5

Edukt 3

HCID 99482-PhenylacetophenoneHCID 14923Ammonium HydroxideHCID 24638Chlorosulfonic acid

Produkt 1

HCID 222857924-(2-Oxo-2-phenylethyl)benzene-1-sulfonamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Chlorosulfonic acid (1781 g, 1018 mL, 15.29 mol) was treated portionwise with deoxybenzoin (400 g, 2.04 mol) at such a rate that the internal temperature was maintained between 5° and 15° C. The mixture was warmed to room temperature and maintained at that temperature for an additional 14 hours. The mixture was poured cautiously into ice water. The crude sulfonyl chloride was filtered and added portionwise to a solution of acetone (600 mL) and concentrated NH4OH (551 mL, 8.15 mol), yielding a pale yellow suspension. The crude precipitate was collected by vacuum filtration, and triturated with boiling acetone (1.5 L). Filtration afforded 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one (162 g, 29%) as an off-white powder: 1H NMR (DMSO-d6, 300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 2H), 7.44 (d, J=8.26, 2H), 7.30 (br s, 2H), 4.52 (s, 2H).

Aufarbeitung

  1. temperaturewas maintained between 5° and 15° C
  2. temperaturemaintained at that temperature for an additional 14 hours
  3. filtrationThe crude sulfonyl chloride was filtered
  4. customyielding a pale yellow suspension
  5. filtrationThe crude precipitate was collected by vacuum filtration
  6. customtriturated with boiling acetone (1.5 L)
  7. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-4b84169acae64933a2ca783eddbe44b2
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859257

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