Acetone → (3,4-Dichlorophenyl)methanesulfonamide

HRID 731393

Reaktionsgleichung

Reaktionsgleichung von HRID 731393
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][S:10](Cl)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)=O.[OH-].[NH4+:19]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][S:10]([NH2:19])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 14923Ammonium HydroxideHCID 2794622(3,4-Dichlorophenyl)methanesulfonyl chloride

Produkt 1

HCID 20472420(3,4-Dichlorophenyl)methanesulfonamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A solution of (3,4-dichloro-phenyl)-methanesulfonyl chloride (500 g, 1.93 mol) and acetone (470 mL) was added over 2 h to cooled (0-5° C.), stirred concentrated ammonium hydroxide (28%, 900 mL, 227 g NH3, 13.3 mol). The reaction mixture was maintained below 12° C. during the addition. The reaction mixture was allowed to warm to room temperature and was stirred for 1 h. Water (900 mL) was added to the reaction mixture and it was stirred for 1 h. The white solid was collected by filtration, washed with cold water (2×500 mL), and vacuum dried to give 375 g (81%) of (3,4-dichloro-phenyl)-methanesulfonamide with 99% purity (as determined by HPLC).

Aufarbeitung

  1. temperatureThe reaction mixture was maintained below 12° C. during the addition
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 1 h
  4. filtrationThe white solid was collected by filtration
  5. washwashed with cold water (2×500 mL), and vacuum
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f0507f5963ea426db87d7ffd1d49254e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582772B2

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