Allyl bromide → HCID 56626424, compound

HRID 2417757Notes

Reaction equation

HRID 2417757 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[NH2:5][N:6]1[C:11](=[O:12])[CH:10]([F:13])[N:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:8]=[C:7]1[SH:18]>[OH-].[Na+].C(Cl)(Cl)Cl>[CH2:1]([S:18][C:7]1[N:6]([NH2:5])[C:11](=[O:12])[CH:10]([F:13])[N:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:8]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 178448763HCID 178448763, compound

Product 1

HCID 56626424HCID 56626424, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

26.6 g (0.22 mol) of allyl bromide were added to a solution of 43.6 g (0.2 mol) of 4-amino-6-fluoro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one in 200 ml of 1 N sodium hydroxide solution at room temperature. The reaction mixture was stirred for approximately 20 hours at room temperature, the organic phase was then taken up in chloroform, and the solution was washed with three times 150 ml of 0.1 N sodium hydroxide solution, dried over sodium sulphate, filtered and concentrated. The oily residue was degassed at 50° C./0.05 mbar, and recrystallized from ethyl acetate/petroleum ether. 20.8 g (40% of theory) of 3-allylthio-4-amino-6-fluoro-tert.-butyl-1,2,4-triazin-5-one of melting point 75° to 74° C. were obtained.

Workup

  1. washthe solution was washed with three times 150 ml of 0.1 N sodium hydroxide solution
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was degassed at 50° C./0.05 mbar
  6. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-a65f8d25abe948d0b908879ad2187c82
Source dataset
uspto-grants-1984_09
Patent number
US04470842

Reaction notes

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