Propargyl bromide → HCID 12534513, compound

HRID 1075178Notes

Reaction equation

HRID 1075178 reaction equation
[K].[CH3:2][S:3][C:4]1[C:9]([F:10])=[CH:8][NH:7][C:6](=[O:11])[N:5]=1.[CH2:12](Br)[C:13]#[CH:14]>CN(C)C=O>[CH2:14]([N:7]1[CH:8]=[C:9]([F:10])[C:4]([S:3][CH3:2])=[N:5][C:6]1=[O:11])[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 5462222PotassiumHCID 178503576HCID 178503576, compound

Product 1

HCID 12534513HCID 12534513, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The potassium salt of 4-methylthio-5-fluoropyrimid-2-one (0.005 mol) and propargyl bromide (0.06 mol) were stirred together in dimethylformamide (20 ml) for 40 hrs at room temperature. The mixture was then filtered; the filtrate evaporated at reduced pressure (1 mm Hg) and the residue extracted with chloroform (60 ml). The chloroform solution was washed with 1 N NaOH, with water, and dried (MgSO4) before evaporation; yield 71%, m.p. 101°-102° C. (ethyl acetate). (Found: C, 48.50; H, 3.62. Calc. for C8H7SN2O: C, 48.48; H, 3.56).

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated at reduced pressure (1 mm Hg)
  3. extractionthe residue extracted with chloroform (60 ml)
  4. washThe chloroform solution was washed with 1 N NaOH, with water
  5. dry with materialdried (MgSO4)
  6. custombefore evaporation

Sources & evidence

ORD record
ord-022e3d27b56145c0855722b24b8f3648
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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