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

HRID 25508

Reaction equation

HRID 25508 reaction equation
[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].[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[F:27])[NH:23][C:22]([C:28]1[CH:29]=[CH:30][C:31]([O:35][CH3:36])=[C:32]([NH2:34])[CH:33]=1)=[CH:21]2.O.Cl>N1C=CC=CC=1>[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[F:27])[NH:23][C:22]([C:28]1[CH:29]=[CH:30][C:31]([O:35][CH3:36])=[C:32]([NH:34][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:33]=1)=[CH:21]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 66280Dodecylsulfonyl chlorideHCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 10300955Dodecane-1-sulfonic acid [5-(5,6-difluoro-1H-indol-2-yl)-methoxy-phenyl]-amideYield 44.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Workup

  1. filtrationAfter several hours the precipitate was filtered off
  2. washrinsed three times with water
  3. customdried
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-d578a370dc0942399ec5b135fdf01bfd
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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