Dimethylformamide → HCID 69519275, compound

HRID 1831323Notes

Reaction equation

HRID 1831323 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:18][N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21].N12CCN(CC1)CC2.CN(C)C=O>O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:20](=[O:21])[N:19]([CH3:18])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178522254HCID 178522254, compound

Product 1

HCID 69519275HCID 69519275, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-benzamide (0.50 g, 2.01 mmol), N-methyl-N-phenylcarbamoyl chloride (0.34 g, 2.01 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.22 g, 0.34 mmol) in dimethylformamide (10 mmol) was stirred at room temperature for 2 hours. Water (100 mL) was added and a thick oil was being formed. The water was decanted and the residue dissolved in dichloromethane, dried over sodium sulphate, filtered and evaporated in vacuo. Ethyl acetate was added and the solution was heated briefly (some of the compound does not dissolve). The solvent was decanted and heptane was added to it. After standing overnight, the crystals were isolated by suction, washed with heptane and dried in a vacuum oven at 45° C. Further purification by flash column chromatography (SiO2, ethyl acetate:heptane 50:50), yielded the title compound (0.41 g, 53% yield) as a white solid.

Workup

  1. customa thick oil was being formed
  2. customThe water was decanted
  3. dissolutionthe residue dissolved in dichloromethane
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. additionEthyl acetate was added
  8. temperaturethe solution was heated briefly (some of the compound
  9. dissolutiondoes not dissolve)
  10. customThe solvent was decanted
  11. additionheptane was added to it
  12. customthe crystals were isolated by suction
  13. washwashed with heptane
  14. customdried in a vacuum oven at 45° C
  15. customFurther purification by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Sources & evidence

ORD record
ord-c502b03dc4654e2c82e6a79c93cd3b69
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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