Toluene → N,4-dimethyl-N-(2-(6-methylpyridin-2-yl)allyl)benzenesulfonamide

HRID 1087949Notes

Reaction equation

HRID 1087949 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH2:22]Cl)=[CH2:21])[N:15]=1.[OH-].[Na+].[C:26]1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][N:2]([CH2:22][C:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH3:26])[N:15]=1)=[CH2:21])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 14798Sodium HydroxideHCID 150087112-Chloro-6-(3-chloroprop-1-en-2-yl)pyridine

Product 1

HCID 15008739N,4-dimethyl-N-(2-(6-methylpyridin-2-yl)allyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
80 °C

Procedure

To a mixture of 1.48 g of N-methyl-p-toluenesulfonamide, 1.0 g of 2-chloro-6-(l-chloromethylvinyl)pyridine (Compound No. I - 3), 0.05 g of tetra-n-butylammonium bromide and 15 ml of toluene, 4.3 g of an aqueous solution of 40% sodium hydroxide was added, and the whole mixture was stirred at 80° C. for 3 hours. The reaction mixture was subsequently washed with water and brine and dried over anhydrous potassium carbonate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluted with benzene - ethyl acetate 15:1) to obtain 1.5 g of Compound No. 216 in Table 6.

Workup

  1. washThe reaction mixture was subsequently washed with water and brine
  2. dry with materialdried over anhydrous potassium carbonate
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (eluted with benzene - ethyl acetate 15:1)

Sources & evidence

ORD record
ord-2bf255e152794e80b8b50bb4724395aa
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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