Reaction #53786

Reaction equation

HCl

1-Dodecanesulfonyl chloride

5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl-amine

5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenylamine

water

→

product

Yield 44.9%

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

Yield 44.9%

Solvents

pyridine

Conditions

Workup

1. 1
   FiltrationAfter several hours the precipitate was filtered off
2. 2
   Washrinsed three times with water
3. 3
   Otherdried
4. 4
   OtherRecrystallization from ethanol

Procedure

1-Dodecanesulfonyl chloride (0.3 g, 1.1 mmol) was added to a stirred solution of 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl-amine from Example 3 (0.3 g, 1.11 mmol) in pyridine (3 mL) under an inert atmosphere at room temperature. After approximately 20 hours the mixture was poured into water (30 mL), stirred, and acidified with aqueous HCl. After several hours the precipitate was filtered off, rinsed three times with water, and dried. Recrystallization from ethanol afforded the product (0.25 g), mp 148-149° C.

Source