Sodium Hydroxide → N-(2-Chloro-5-iodopyridin-4-yl)methanesulfonamide

HRID 2205857Notes

Reaction equation

HRID 2205857 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8](S(C)(=O)=O)[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([I:17])=[CH:4][N:3]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([I:17])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86706271N-(2-Chloro-5-iodopyridin-4-yl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 86706272N-(2-Chloro-5-iodopyridin-4-yl)methanesulfonamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

N-(2-chloro-5-iodopyridin-4-yl)-N-(methylsulfonyl)methanesulfonamide (13) (1.1 g) was stirred with THF (6.8 mL) and 10% sodium hydroxide (6.8 mL) at room temperature overnight. The THF was evaporated and the aqueous was brought to pH about 5 with 10% citric acid solution. Product was deposited—the mixture was cooled at 0-5° C. for 0.5 h and the product filtered off. It was washed with a little water and dried over sodium hydroxide in a vacuum desiccator to give the title compound (772 mg, 83%). 1H-NMR (500 MHz, DMSO-d6): 3.29 (s, 3H), 7.42 (s, 1H), 8.66 (s, 1H).

Workup

  1. customThe THF was evaporated
  2. filtrationthe product filtered off
  3. washIt was washed with a little water
  4. dry with materialdried over sodium hydroxide in a vacuum desiccator

Sources & evidence

ORD record
ord-f28b069d62fc4c47bdd6015c202ba09c
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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