Dimethylcarbamoyl Chloride → 4-Isopropylpicolinonitrile

HRID 2070924Notes

Reaction equation

HRID 2070924 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Si]([C:15]#[N:16])(C)(C)C.CN(C)C(Cl)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:15]#[N:16])[CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 3156064-Isopropyl-pyridine 1-oxide

Product 1

HCID 450794854-Isopropylpicolinonitrile

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 139 mg (1.01 mmol) of 4-isopropylpyridine N-oxide in 10 mL of CH2Cl2 at r.t. was added 160 μL (1.20 mmol) of TMSCN. After 5 min., 100 μL (1.09 mmol) of dimethylcarbamyl chloride was added, and the solution was stirred at r.t. for 16 h. The solution was diluted with chloroform and washed with 20 mL of 10% aqueous K2CO3. The layers were separated, and the aqueous layer was extracted 3 times with CHCl3. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 4-isopropylpicolinonitrile with some impurity as a liquid.

Workup

  1. washwashed with 20 mL of 10% aqueous K2CO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted 3 times with CHCl3
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-57fa147eeac14ca19f137fae5cf20232
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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