Dimethylcarbamoyl Chloride → 4-Pentyl-2-cyanopyridine

HRID 1374468

Reaction equation

HRID 1374468 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7](OC1C=C[N+]([O-])=CC=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:22][N:23]([CH3:27])C(Cl)=O.[C:28](=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:11]([C:10]1[CH:9]=[CH:27][N:23]=[C:22]([C:5]#[N:6])[CH:28]=1)[CH2:12][CH2:13][CH2:8][CH3:7]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 2958714-(Benzyloxy)pyridine N-oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 210760834-Pentyl-2-cyanopyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To trimethylsilyl cyanide (5.2 g, 52 mmol), 4-benzyloxy-pyridine 1-oxide (8.8 g, 44 mmol) in DCM (20 mL) was added, followed by dimethylcarbamoyl chloride (5.6 g, 52 mmol) in DCM (10 mL), dropwise, stirred at room temperature overnight. Sodium bicarbonate (100 mL, 10%) was added, stirred for 10 minutes and extracted twice with DCM (50 mL). The combined organic layer was dried over magnesium sulfate, solvent was removed to obtain the product, compound 10a (R9=Benzyloxy) (10.5 g, 100%).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted twice with DCM (50 mL)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate, solvent
  4. customwas removed

Sources & evidence

ORD record
ord-8ff36099531048408abe54de9026d0ee
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Linked notes

Loading…