Cesium carbonate → HCID 59202007, compound

HRID 1096553Notes

Reaction equation

HRID 1096553 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[N:12][C:13]#[N:14])[CH3:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25].[I-].[Cs+]>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])[C:10](=[N:12][C:13]#[N:14])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 126424063-Bromo-1,1-dichloroprop-1-eneHCID 178464613HCID 178464613, compound

Product 1

HCID 59202007HCID 59202007, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

174 mg (0.83 mmol) of N-[(6-chloropyridin-3-yl)methyl]-N′-cyanoethanimidamide are stirred into 5 ml of acetonitrile, and 543 mg (1.67 mmol) of cesium carbonate, 166 mg (0.88 mmol) of 3-bromo-1,1-dichloroprop-1-ene and 22 mg (0.08 mmol) of cesium iodide are added successively. The reaction mixture is then stirred at room temperature for 1 hour. The reaction mixture is concentrated under reduced pressure and then taken up in ethyl acetate, washed successively with 1 N aqueous hydrochloric acid, 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 215 mg (77% of theory) of N-[(6-chloropyridin-3-yl)methyl]-N′-cyano-N-(3,3-dichloroprop-2-en-1-yl)ethanimidamide

Workup

  1. additionare added successively
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washwashed successively with 1 N aqueous hydrochloric acid, 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customConcentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel using the mobile phase mixture ethyl acetate:cyclohexane (2:1)

Sources & evidence

ORD record
ord-4a010222385940d18eab9e3636c39de0
Source dataset
uspto-grants-2012_03
Patent number
US08138350B2

Reaction notes

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