Toluene → HCID 86739616, compound

HRID 2417756Notes

Reaction equation

HRID 2417756 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[NH2:5][N:6]1[C:11](=[O:12])[CH:10]([Cl:13])[N:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:8]=[C:7]1[SH:18].[OH-].[Na+].C1(C)C=CC=CC=1>O.[Br-].C([P+](CCCC)(CCCC)CCCC)CCCC>[NH2:5][N:6]1[C:11](=[O:12])[CH:10]([Cl:13])[N:9]([C:14]([CH3:15])([CH3:17])[CH3:16])[N:8]=[C:7]1[S:18][CH2:3][C:2]#[CH:1]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 178448762HCID 178448762, compound

Product 1

HCID 86739616HCID 86739616, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 20446536HCID 20446536, compoundCatalystHCID 962WaterSolvent

Procedure

18.6 g (80% stength solution in toluene=0.125 mol) of propargyl bromide and 0.5 g of pentyltributylphosphonium bromide were added to a solution of 23.5 g (0.1 mol) of 4-amino-6-chloro-tert.-butyl-3-mercapto-1,2,4-triazin-5-one and 4.4 g of sodium hydroxide in 40 ml of water. The reaction mixture was stirred for about 20 hours at room temperature, 100 ml of toluene were then added, and the mixture was filtered. The filtrate was washed with 100 ml of water, with 100 ml of 1 N sodium hydroxide solution and again with water. The organic phase was dried over sodium sulphate, filtered and concentrated. The oily residue was brought to crystallization by trituration in diisopropyl ether, and the product was recrystallized from ethyl acetate/petroleum ether. 13.8 g (57.5% of theory) of 4-amino-6-chloro-tert.-butyl-3-propargylthio-1,2,4-triazin-5-one of melting point 107°-108° C. were obtained.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with 100 ml of water, with 100 ml of 1 N sodium hydroxide solution and again with water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oily residue was brought to crystallization by trituration in diisopropyl ether
  7. customthe product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-798bed02bf6d47f6aa49db37a820eb1e
Source dataset
uspto-grants-1984_09
Patent number
US04470842

Reaction notes

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