Hydroxylamine → HCID 54212349, compound

HRID 984039Notes

Reaction equation

HRID 984039 reaction equation
O(C)[Na].[NH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:22]#[N:23]>C(O)C>[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[CH:15]=[N:14]2)[CH:10]=[CH:9][C:8]=1[CH:21]([C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[C:22](=[N:4][OH:5])[NH2:23]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 58901ClazurilHCID 178418582HCID 178418582, compound

Product 1

HCID 54212349HCID 54212349, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

NaOCH3 (0.189 mol; 30% in CH3OH) was added to a solution of hydroxylamine (0.189 mol) in ethanol (105 ml) The mixture was stirred at RT for 15 minutes and then filtered. The filtrate was added to a mixture of 2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2-(3H)-yl)benzeneacetonitrile (0.054 mol) in ethanol (55 ml). The mixture was stirred at 60° C. for 1 hour, stirred and refluxed for 2 hours and stirred at RT overnight. The solvent was evaporated. The residue was taken up in water and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 20.3 g of (±)-2-chloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-N′-hydroxybenzeneethanimidamide (interm. 66).

Workup

  1. filtrationfiltered
  2. stirringThe mixture was stirred at 60° C. for 1 hour
  3. stirringstirred
  4. temperaturerefluxed for 2 hours
  5. stirringstirred at RT overnight
  6. customThe solvent was evaporated
  7. extractionextracted with EtOAc
  8. customThe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f4adf5f9e23540ed891f4c8c0cbbf82e
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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