Реакция #53789

Уравнение реакции

HCl

1-Dodecanesulfonyl chloride

5-(5,6-dichloro-1H-benzoimidazol-2-yl)-2-methoxy-phenylamine

water

→

product

Выход 4.0%

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

Выход 4.0%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred
2. 2
   ЭкстракцияAfter several hours the mixture was extracted with dichloromethane (60 mL, 30 mL)
3. 3
   Промывкаthe combined extracts were washed with water
4. 4
   workup.ADDITIONA little saturated brine was added
5. 5
   ПромывкаThe organic phase was washed with saturated brine
6. 6
   Сушкаdried over MgSO4
7. 7
   Другоеto leave the crude product as a crystalline residue
8. 8
   ДругоеRecrystallization from acetonitrile

Методика

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.

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