Hydrochloric Acid → 3-(Dodecane-1-sulfonylamino)-4-methoxy-N-(3,4-dichloro-phenyl)-benzamide

HRID 1859752

Reaktionsgleichung

Reaktionsgleichung von HRID 1859752
N1C=CC=CC=1.[CH2:7]([S:19](Cl)(=[O:21])=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)=[O:28].Cl>O>[CH2:7]([S:19]([NH:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)=[O:28])(=[O:21])=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 66280Dodecylsulfonyl chlorideHCID 99486273-Amino-4-methoxy-N-(3,4-dichlorophenyl)-benzamide

Produkt 1

HCID 186263143-(Dodecane-1-sulfonylamino)-4-methoxy-N-(3,4-dichloro-phenyl)-benzamideAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Pyridine (5 mL) was added to a mixture of 1-dodecane-sulfonyl chloride (Maybridge) (0.8 g, 3.0 mmol) and 3-amino-4-methoxy-N-(3,4-dichloro-phenyl)-benzamide from Example 4 (0.73 g, 3.0 mmol) and stirred at room temperature. After 5 days the mixture was heated on a steambath for 1.5 hours, allowed to cool, and added to water (150 mL), acidified with 4N HCl, and stirred for an hour. The precipitate was filtered off, rinsed with water then with ethanol and dried to afford the product (1.3 g); m.p. 151-152° C. after recrystallization from ethanol and chromatography on silica gel in CHCl3/EtOAc (9:1).

Aufarbeitung

  1. temperatureAfter 5 days the mixture was heated on a steambath for 1.5 hours
  2. temperatureto cool
  3. stirringstirred for an hour
  4. filtrationThe precipitate was filtered off
  5. washrinsed with water
  6. dry with materialwith ethanol and dried

Quellen und Nachweise

ORD-Eintrag
ord-fd606becb84f46d680e6f26fc11eb501
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528528B2

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