Hydroxylamine → HCID 54210833, compound

HRID 1370252Notes

Reaction equation

HRID 1370252 reaction equation
[NH2:1][OH:2].[C:3]1([C:9]2([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[O:14][CH2:13]C=[CH:11][O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C>C(O)C>[OH:2][N:1]=[C:19]([C:18]1[CH:17]=[CH:16][C:15]([C:9]2([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:14][CH2:13][CH2:11][O:10]2)=[CH:22][CH:21]=1)[NH2:20]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8471TriethylamineHCID 18510671HCID 18510671, compound

Product 1

HCID 54210833HCID 54210833, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

) Hydroxylamine (0.0449 mol) was added to a mixture of 4-(2-phenyl-1,3-dioxin-2-yl)benzonitrile (0.022 mol) in ethanol (88 ml). Then, N,N-diethylethanamine (0.0449 mol) was added dropwise and the resulting reaction mixture was stirred and refluxed for 3.5 hours. The solvent was evaporated. The residue was washed with water and this mixture was extracted with EtOAc. The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated, yielding 6.38 g of N′-hydroxy-4-(2-phenyl-1,3-dioxolan-2-yl)benzenecarboimidamide (interm. 10)

Workup

  1. customthe resulting reaction mixture
  2. temperaturerefluxed for 3.5 hours
  3. customThe solvent was evaporated
  4. washThe residue was washed with water
  5. extractionthis mixture was extracted with EtOAc
  6. dry with materialThe separated organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-58919a9a9edd4252a7bc2b3cd9094a03
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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