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

HRID 556328Notes

Reaction equation

HRID 556328 reaction equation
[H-].[Na+].CN(C)C=O.[F:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[N:13][CH:14]=1.I[CH2:27][C:28]([NH2:30])=[O:29]>O>[F:8][C:9]1[CH:10]=[CH:11][C:12](=[N:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[N:13]([CH2:27][C:28]([NH2:30])=[O:29])[CH:14]=1

Participants

6

Reactant 4

HCID 3727IodoacetamideHCID 6228DimethylformamideHCID 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 1

HCID 962WaterSolvent

Procedure

Sodium hydride (0.43 g, 0.018 mol) was mixed with N,N-Dimethylformamide (67.4 mL) and N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide 1 (4.0 g, 0.015 mol) was added. The reaction was stirred at room temperature for 10 minutes. Iodoacetamide (3.3 g, 0.018 mol) was added and the mixture was stirred at room temperature for 24 hours. The reaction was poured into water (100 mL) and extracted with ethyl acetate (4×75 mL). Organic layers were combined then dried with magnesium sulfate and the solvent removed. The crude product was chromatographed on silica using 5% methanol in dichloromethane to give 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)acetamide 2 Rf 0.26, 5% methanol.dichloromethane; MS m/z 324 (M+H)

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. extractionextracted with ethyl acetate (4×75 mL)
  4. dry with materialOrganic layers were combined then dried with magnesium sulfate
  5. customthe solvent removed
  6. customThe crude product was chromatographed on silica using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-e16d05dad7154720920ce03dbd324250
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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