Benzenesulfonyl chloride → HCID 23501220, compound

HRID 1835919Notes

Reaction equation

HRID 1835919 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[C:18]1([S:24]([Cl:27])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[ClH:27].[C:18]1([S:24]([N:1]2[C:9]3[C:4](=[C:5]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 23501285HCID 23501285, compound

Product 1

HCID 23501220HCID 23501220, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(1H-indol-4-yloxy)ethyl dimethylamine (0.300 g, 0.0015 mol), tetrabutylammonium hydrogen sulfate (0.025 g, 0.000073 mol) and finely ground sodium hydroxide (0.065 g, 0.0016 mol) in 20 mL of CH2Cl2 at 0° C. was added benzenesulfonyl chloride (0.286 g, 0.0016 mol). After 18 hours stirring at ambient temperature, the reaction mixture was diluted with 40 mL of CH2Cl2 and washed sequentially with water (2×20 mL) and an aqueous K2CO3 solution (2 M, 20 mL). The aqueous layers were combined and extracted with CH2Cl2 (2×20 mL). The organic fractions were combined, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10:89.9:0.1 methanol/ethyl acetate/ammonium hydroxide) and the resulting oil was dissolved in boiling 10% ethanolic HCl (3 mL). From this solution, 2-(1-benzenesulfonyl-1H-indol-4-yloxy)ethyl dimethylamine hydrochloride salt was crystallized as a fine pink crystal (0.150 mg, 26%). MS: (M+H)+=345, mp 136-140° C.

Workup

  1. washwashed sequentially with water (2×20 mL)
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (10:89.9:0.1 methanol/ethyl acetate/ammonium hydroxide)
  6. dissolutionthe resulting oil was dissolved
  7. customFrom this solution, 2-(1-benzenesulfonyl-1H-indol-4-yloxy)ethyl dimethylamine hydrochloride salt was crystallized as a fine pink crystal (0.150 mg, 26%)

Sources & evidence

ORD record
ord-57f603f025834062b280568a1c40244c
Source dataset
uspto-grants-2004_08
Patent number
US06774241B2

Reaction notes

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