4-Toluenesulfonyl chloride → 4-Methyl-N-pyridin-2-ylmethyl-benzenesulfonamide

HRID 1728857Notes

Reaction equation

HRID 1728857 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 516892Sodium Bicarbonate

Product 1

HCID 7316234-Methyl-N-pyridin-2-ylmethyl-benzenesulfonamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 15.0 g of 2-(aminomethyl)pyridine, 15.44 g of triethylamine and 150 ml of methylene chloride is added 29.1 g of p-toluenesulfonyl chloride in 100 ml of methylene chloride. The reaction mixture is allowed to warm to room temperature and is stirred for 4.5 hours. The solution is poured into saturated sodium bicarbonate and extracted with methylene chloride. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 50% ethyl acetate/hexane 20% methyl alcohol/ethyl acetate); then recrystallized from ethyl acetate/hexane to give 25.9 g of the desired product as colorless crystals.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers are washed with saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography (silica gel: 50% ethyl acetate/hexane 20% methyl alcohol/ethyl acetate)
  6. customthen recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-35b2a01ae8fc4aedb5fe302b25c32327
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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