Dimethylcarbamoyl Chloride → HCID 22494275, compound

HRID 1816592Notes

Reaction equation

HRID 1816592 reaction equation
[CH3:1][N:2](C)C(Cl)=O.C([O-])(=O)CCCCCCC/C=C\CCCCCCCC.[CH2:27]([O:29][C:30](=[O:43])[CH:31]([O:39][CH:40]([CH3:42])[CH3:41])[CH2:32][C:33]1[CH:38]=[CH:37][NH+:36]=[CH:35][CH:34]=1)[CH3:28].C[Si](C#N)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([C:37]1[CH:38]=[C:33]([CH2:32][CH:31]([O:39][CH:40]([CH3:42])[CH3:41])[C:30]([O:29][CH2:27][CH3:28])=[O:43])[CH:34]=[CH:35][N:36]=1)#[N:2]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 69801129HCID 69801129, compound

Product 1

HCID 22494275HCID 22494275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.3 mL dimethyl carbamyl chloride was added dropwise over 40 minutes into a solution of 6.40 g crude 4-(3-ethoxy-2-isopropoxy-3-oxopropyl)-1-pyridinium oleate and 3.3 mL trimethylsilyl cyanide in dichloromethane (60 mL), followed by stirring for 11.5 hours. 10% aqueous potassium carbonate was added to the reaction solution, followed by stirring at room temperature for 30 minutes. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography, to give 3.87 g of ethyl 3-(2-cyano-4-pyridyl)-2-isopropoxypropanoate as a pale yellow oil.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-e7fbc273b335441fa0e87c8d899086ff
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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