Hydroxylamine → HCID 58404362, compound

HRID 1172952Notes

Reaction equation

HRID 1172952 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])([CH3:3])[CH3:2].[NH2:17][OH:18]>CCO>[OH:18]/[N:17]=[C:9](\[NH2:10])/[C:8]1[CH:11]=[CH:12][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58404446HCID 58404446, compound

Product 1

HCID 58404362HCID 58404362, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an atmosphere of nitrogen, 4-isopropoxy-3-(trifluoromethyl)benzonitrile (6.5 g, 28.4 mmol) and 50% aqueous hyroxylamine (5.21 mL, 85 mmol) in EtOH (20.0 mL) was heated at 60° C. for 18 hr. Solvents removed in vacuo and the residue was azeotroped with MeOH. The residual solid was purified by precipitation from an ethyl acetate/30-600 C pet/ether mixture (1:2) to give (Z)-N′-hydroxy-4-isopropoxy-3-(trifluoromethyl)benzimidamide (2.51 g, 33.8%) LCMS (Table 1, Method b) Rt=1.89 min, m/z 263.13 (M+H)+.

Workup

  1. customSolvents removed in vacuo
  2. customthe residue was azeotroped with MeOH
  3. customThe residual solid was purified by precipitation from an ethyl acetate/30-600 C pet/ether mixture (1:2)

Sources & evidence

ORD record
ord-0b0de4ff901a424c970f120373117780
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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