Water → N'-[5-(4-chlorobutoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylimidoformamide

HRID 749173Notes

Reaction equation

HRID 749173 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([OH:11])=[CH:5][C:4]=1[N:12]=[CH:13][N:14]([CH3:16])[CH3:15])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][Cl:28].O>CN(C)C=O>[Cl:28][CH2:27][CH2:26][CH2:25][CH2:24][O:11][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([C:1]#[N:2])=[C:4]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 11644225HCID 11644225, compound

Product 1

HCID 68993086N'-[5-(4-chlorobutoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylimidoformamideYield 796.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N′-(2-cyano-5-hydroxy-4-methoxyphenyl)-N,N-dimethylimidoformamide (3.29 g, 1.5 mmol) in dimethylformamide (33 ml) and potassium carbonate (4.14 g, 30 mmol) was reacted with 1-bromo 4-chorobutane (3.86 g, 2.5 mmol) at 60° C. for 2 hours. Water was added to the reaction mixture which was then extracted with ethyl acetate. The organic phase was dried (magnesium sulphate), concentrated and the residue was purified by chromatography on silica gel. Elution with dichloromethane:ethyl acetate (8:2) then increased polarity to (6:4) yielded N′-[5-(4-chlorobutoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylimidoformamide as a white solid (3.7 g, 80% yield):

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (magnesium sulphate)
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel
  5. washElution with dichloromethane:ethyl acetate (8:2)
  6. temperaturethen increased polarity to (6:4)

Sources & evidence

ORD record
ord-ac84760a64974214b0fa3b1170199903
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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