Propargyl bromide → HCID 13279245, compound

HRID 542382Notes

Reaction equation

HRID 542382 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9](=[O:12])[CH2:10][Cl:11])=[C:6]([CH3:13])[N:5]=[CH:4][N:3]=1.[CH2:14](Br)[C:15]#[CH:16].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH2:16]([N:8]([C:7]1[C:6]([CH3:13])=[N:5][CH:4]=[N:3][C:2]=1[CH3:1])[C:9](=[O:12])[CH2:10][Cl:11])[C:15]#[CH:14]

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 15585339HCID 15585339, compound

Product 1

HCID 13279245HCID 13279245, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.0 g (0.025 mol) N-(4,6-dimethylpyrimidin-5-yl)-chloroacetamide and 1.0 g tetrabutylammoniumchloride in 150 ml CH2Cl2 and 6.0 g propargylbromide is cooled to 8°, and 15 ml 50% aqueous NaOH are added dropwise thereto, whereby the temperature gradually rises to 20°. The reaction temperature is maintained at 18° to 20° with cooling. The mixture is stirred during 21/2 hours and then diluted with 100 ml H2O. The organic phase is separated off and dried over Na2SO4. The dried solution is evaporated to give a brown powder that is chromatographed on silica gel with the aid of diethylether (Rf=0.15), yielding the title compound in the form of white crystals m.p. 122°-123°.

Workup

  1. temperatureis cooled to 8°
  2. customgradually rises to 20°
  3. temperatureThe reaction temperature is maintained at 18° to 20°
  4. temperaturewith cooling
  5. customThe organic phase is separated off
  6. dry with materialdried over Na2SO4
  7. customThe dried solution is evaporated
  8. customto give a brown powder that
  9. customis chromatographed on silica gel with the aid of diethylether (Rf=0.15)

Sources & evidence

ORD record
ord-71ea017638fc4256834973164e506f99
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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