Triethylamine → N-(pyridin-2-ylmethyl)methanesulfonamide

HRID 1728887Notes

Reaction equation

HRID 1728887 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.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][S:17]([CH3:16])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 4657001N-(pyridin-2-ylmethyl)methanesulfonamideYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° solution of 15 g of 2-(aminomethyl)pyridine, 15.44 g of triethylamine and 150 ml of methylene chloride is added 17.48 g of methanesulfonyl chloride in 100 ml of methylene chloride. The mixture is stirred at 0° C. for 1 hour followed by stirring at room temperature for 3 hours. The reaction is poured into saturated sodium bicarbonate and extracted with methylene chloride. The combined extracts are washed with saturated sodium chloride and concentrated in vacuo. The residue is purified by chromatography (silica gel: 10% methyl alcohol/ethyl acetate) to give 19.84 g of the desired product.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with saturated sodium chloride
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel: 10% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-ef97c1b6879e4165abc59e5e58371220
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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