Pyridine → HCID 11404180, compound

HRID 1794586Notes

Reaction equation

HRID 1794586 reaction equation
[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]([NH:8][N:9]1[C:13](I)=[C:12]([CH3:15])[N:11]=[C:10]1[CH2:16][CH2:17][CH3:18])=[O:7])[CH3:2].[Cu][C:24]#[N:25].N1C=CC=CC=1>ClCCl>[C:24]([C:13]1[N:9]([NH:8][C:6](=[O:7])[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[O:3][CH2:1][CH3:2])[C:10]([CH2:16][CH2:17][CH3:18])=[N:11][C:12]=1[CH3:15])#[N:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11269925HCID 11269925, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 11404180HCID 11404180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Ethoxy-N-(5-iodo-4-methyl-2-propylimidazol-1-yl)benzamide from Example 1a (0.5 g, 1.2 mmol) and copper(I) cyanide (0.7 g, 7.5 mmol) are introduced into 10 ml of pyridine and heated at 100° C. for three hours. The reaction mixture is cooled to room temperature, 50 ml of dichloromethane are added, and the solid is removed by filtration. The filtrate is washed three times with 50 ml of water each time, and the organic phase is re-extracted with 50 ml of dichloromethane. The combined organic phase is dried with sodium sulphate and concentrated. To remove the remaining pyridine, the residue is taken up in 50 ml of dichloromethane and washed six times with 100 ml of water each time. The organic phase is dried with sodium sulphate and concentrated in a rotary evaporator. The residue is finally mixed with 100 ml of toluene and concentrated.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe solid is removed by filtration
  3. washThe filtrate is washed three times with 50 ml of water each time
  4. extractionthe organic phase is re-extracted with 50 ml of dichloromethane
  5. dry with materialThe combined organic phase is dried with sodium sulphate
  6. concentrationconcentrated
  7. customTo remove the remaining pyridine
  8. washwashed six times with 100 ml of water each time
  9. dry with materialThe organic phase is dried with sodium sulphate
  10. concentrationconcentrated in a rotary evaporator
  11. additionThe residue is finally mixed with 100 ml of toluene
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-2a36c94fa61e4ed1ac847e6bc3e4f08b
Source dataset
uspto-grants-2006_04
Patent number
US07022847B2

Reaction notes

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