Pyridine → N-[4-chloro-2-(2-chlorobenzyl)phenyl]-3-methoxybenzenesulfonamide

HRID 747611Notes

Reaction equation

HRID 747611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1.N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[CH:26]=2)(=[O:33])=[O:32])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 143578744-Chloro-2-[(2-chlorophenyl)methyl]aniline

Product 1

HCID 68565360N-[4-chloro-2-(2-chlorobenzyl)phenyl]-3-methoxybenzenesulfonamideYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Starting with 0.71 g of [4-chloro-2-(2-chlorobenzyl)phenyl]amine dissolved in 5 ml of THF are added 0.4 ml of pyridine and 0.8 g of 3-methoxybenzenesulfonyl chloride, and the mixture is left at room temperature for 18 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) cyclohexane/ethyl acetate solvent mixture to give 0.666 g of expected product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on a column of silica gel
  5. washeluting with a 90/10 (v/v) cyclohexane/ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-3c9ab68c341247d0b0b236e22bf92e09
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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