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

HRID 1971631Notes

Reaction equation

HRID 1971631 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-3067aa372e1d427eb0a7cbca69324241
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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