Sodium hydride → HCID 15586997, compound

HRID 544529Notes

Reaction equation

HRID 544529 reaction equation
[CH3:1][S:2][C:3]1[NH:4][N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:7](=[O:9])[N:8]=1.[H-].[Na+].[H][H].C1(C)C=C(C)C=C(C)C=1S([NH:32]O)(=O)=O>CN(C)C=O>[NH2:32][N:4]1[C:3]([S:2][CH3:1])=[N:8][C:7](=[O:9])[C:6]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:5]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 11009332O-mesitylenesulfonylhydroxylamineHCID 178418361HCID 178418361, compoundHCID 178503529HCID 178503529, compound

Product 1

HCID 15586997HCID 15586997, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methylthio-6-(p-fluorophenyl)-5-oxo-2,5-dihydro-1,2,4-triazine (2.5 g) in anhydrous dimethylformamide (50 ml), sodium hydride (50% dispersion, 0.5 g) was gradually added and stirred until the generation of hydrogen gas was not detected. o-Mesitylenesulfonylhydroxylamine (2.1 g) was added to the mixture, followed by stirring at room temperature for 6 hours. After completion of the reaction, the resultant mixture was poured into ice-water. The precipitated crystals were collected by filtration. Recrystallization of the obtained crystals from methanol gave 2.0 g of 2-amino-3-methylthio-6-(p-fluorophenyl)-5-oxo-2,5-dihydro-1,2,4-triazine in 74% yield. M.P., 192° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationThe precipitated crystals were collected by filtration
  3. customRecrystallization of the obtained crystals from methanol

Sources & evidence

ORD record
ord-f84ee8f086754f6c87c4c9fad2b196a8
Source dataset
uspto-grants-1984_05
Patent number
US04451283

Reaction notes

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