Iodoacetamide → 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)acetamide

HRID 1971615Notes

Reaction equation

HRID 1971615 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:8][CH:9]=1.I[CH2:22][C:23]([NH2:25])=[O:24]>CN(C)C=O.C(OCC)(=O)C.O>[F:3][C:4]1[CH:5]=[CH:6][C:7](=[N:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:8]([CH2:22][C:23]([NH2:25])=[O:24])[CH:9]=1

Participants

7

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 57607460N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

Product 1

HCID 669919052-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (5.0 g, 0.21 mol) in N,N-Dimethylformamide (370 mL) was treated portion wise with N-(5-Fluoro-pyridin-2-yl)-4-methyl-benzenesulfonamide (compound a, 50 g, 0.2 mol). After stirring for 20 minutes, iodoacetamide (30 g, 0.2 mol) was added in one portion. The reaction stirred overnight at room temperature. The solvent was removed to give a brown solid. The crude material was diluted with 500 ml of ethyl acetate and 100 mL of water and stirred for 2 hours. The solid was collected by filtration and dried to afford 36 g of 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)acetamide. Rf 0.37, neat ethyl acetate MS m/z 324 (M+H).

Workup

  1. stirringThe reaction stirred overnight at room temperature
  2. customThe solvent was removed
  3. customto give a brown solid
  4. stirringstirred for 2 hours
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-cc077e124a494c6bb1b5263ee933eba0
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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