O-Methylhydroxylamine → 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-methoxy-2-(2-phenylphenyl)sulfonylguanidine

HRID 1589092Notes

Reaction equation

HRID 1589092 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH:10][C:11](=[N:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][CH3:24])[N:16]=1)SC)(=[O:9])=[O:8].[CH3:31][O:32][NH2:33]>O1CCOCC1>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([NH:10][C:11]([NH:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][CH3:24])[N:16]=1)=[N:33][O:32][CH3:31])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 4113O-MethylhydroxylamineHCID 178494236HCID 178494236, compound

Product 1

HCID 1785028681-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-methoxy-2-(2-phenylphenyl)sulfonylguanidineYield 69.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.45 g of 1-(2-biphenylylsulfonyl) 3-(4,6-dimethoxy-1,3,5-triazin-2-yl) 2-methylisothiourea were dissolved in 50 ml of dioxane, and 2.35 g of O-methylhydroxylamine were added to the solution. The mixture was heated under reflux for 5 hours. After cooling, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to give 3.1 g of N-(2-biphenylylsulfonyl) N'-(4,6-dimethoxy-1,3,5-triazin-2-yl) N"-(methoxy)guanidine represented by the following formula: ##STR30##

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-99a223963c9c461a9a88f346e86a460e
Source dataset
uspto-grants-1986_02
Patent number
US04568381

Reaction notes

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