Hydrochloric Acid → Dodecane-1-sulfonic acid [5-(5,6-dichloro-1H-benzoimidazol-2-yl)-2-methoxy-phenyl]-amide

HRID 25511

Reaktionsgleichung

Reaktionsgleichung von HRID 25511
[CH2:1]([S:13](Cl)(=[O:15])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:17][C:18]1[C:35]([Cl:36])=[CH:34][C:21]2[NH:22][C:23]([C:25]3[CH:26]=[CH:27][C:28]([O:32][CH3:33])=[C:29]([NH2:31])[CH:30]=3)=[N:24][C:20]=2[CH:19]=1.O.Cl>N1C=CC=CC=1>[Cl:36][C:35]1[C:18]([Cl:17])=[CH:19][C:20]2[NH:24][C:23]([C:25]3[CH:26]=[CH:27][C:28]([O:32][CH3:33])=[C:29]([NH:31][S:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:15])=[O:14])[CH:30]=3)=[N:22][C:21]=2[CH:34]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 66280Dodecylsulfonyl chlorideHCID 225684435-(5,6-Dichloro-1H-benzo[d]imidazol-2-yl)-2-methoxyaniline

Produkt 1

HCID 10165774Dodecane-1-sulfonic acid [5-(5,6-dichloro-1H-benzoimidazol-2-yl)-2-methoxy-phenyl]-amideAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-Dodecanesulfonyl chloride (0.38 g, 1.4 mmol) was added to a stirred suspension of 5-(5,6-dichloro-1H-benzoimidazol-2-yl)-2-methoxy-phenylamine from Step B (0.6 g, 1.4 mmol) in pyridine (6 mL) under an inert atmosphere, warmed briefly to 80° C. then stirred at room temperature. After approximately 20 hours the mixture was poured into water (60 mL), stirred, and acidified with aqueous HCl. After several hours the mixture was extracted with dichloromethane (60 mL, 30 mL) and the combined extracts were washed with water then 0.5 M sodium bicarbonate solution. A little saturated brine was added to assist with stratification. The organic phase was washed with saturated brine, dried over MgSO4, and stripped of solvent to leave the crude product as a crystalline residue. Recrystallization from acetonitrile followed by chromatography on silicagel in CHCl3/EtOAc (9:1) afforded the product (0.03 g), mp 203-204° C.

Aufarbeitung

  1. stirringstirred
  2. extractionAfter several hours the mixture was extracted with dichloromethane (60 mL, 30 mL)
  3. washthe combined extracts were washed with water
  4. additionA little saturated brine was added
  5. washThe organic phase was washed with saturated brine
  6. dry with materialdried over MgSO4
  7. customto leave the crude product as a crystalline residue
  8. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-7350282654234993b67851b90c324ce6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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