Dimethylcarbamoyl Chloride → HCID 19864572, compound

HRID 1200035Notes

Reaction equation

HRID 1200035 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][N+:8]([O-])=[CH:7][C:6]=1[C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH3:4].C[Si]([C:19]#[N:20])(C)C.CN(C)C(Cl)=O>ClCCl>[CH2:1]([C:5]1[C:6]([C:12]([OH:14])=[O:13])=[CH:7][N:8]=[C:9]([C:19]#[N:20])[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 54003163HCID 54003163, compound

Product 1

HCID 19864572HCID 19864572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-n-butyl-3-carboxy-pyridine N-oxide (600 mg, 3 mmol) in 15 ml of dichloromethane is added trimethylsilylcyanide (595 mg, 6 mmol), and the solution is stirred for 5 min. Then dimethylcarbamoyl chloride (645 mg, 6 mmol) is added and stirring continued for 4 days under reflux. After cooling, the solution is evaporated to dryness under reduced pressure, and the residue is purified by column chromatography (dichloromethane/methanol 3:1) to yield 4-n-butyl-5-carboxy-2-cyano-pyridine, m.p. 267°-268°, Rf =0.3.

Workup

  1. stirringstirring
  2. waitcontinued for 4 days
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe solution is evaporated to dryness under reduced pressure
  6. customthe residue is purified by column chromatography (dichloromethane/methanol 3:1)

Sources & evidence

ORD record
ord-5e4da3da6ee64032855cf80af33fb5e4
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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