Sodium hydride → N-Methyl-N-[4-picolyl]formamide

HRID 325107Notes

Reaction equation

HRID 325107 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[CH3:10][NH:11][CH:12]=[O:13].[H-].[Na+]>C1COCC1>[CH3:10][N:11]([CH:12]=[O:13])[CH2:8][C:5]1[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31254N-MethylformamideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 15893405N-Methyl-N-[4-picolyl]formamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring, argon-purged solution of 4-picolyl chloride-HCl (15 g, 91.4 mmol) and N-methylformamide (53.4 ml, 914 mmol) in 300 ml of THF at room temperature was added portionwise over a 20 minute period a suspension of 80% NaH (5.48 g, 183 mmol). The reaction was quenched 18 h later by the addition of ice, partitioned between methylene chloride and water, washed with water and brine, dried over MgSO4, and evaporated to dryness to afford a dark oil. Flash chromatography on silica gel provided 10.5 g (76%) of the titled compounds a pale yellow oil. TLC; silica gel (9:1 CHCl/MeOH) Rf=0.54.

Workup

  1. additionwas added portionwise over a 20 minute period
  2. customThe reaction was quenched 18 h later by the addition of ice
  3. custompartitioned between methylene chloride and water
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customto afford a dark oil

Sources & evidence

ORD record
ord-d56ea18a74ee4fc19405ae563d58861a
Source dataset
uspto-grants-2001_04
Patent number
US06222036B1

Reaction notes

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