Hydroxylamine → N'-Hydroxybenzenecarboximidamide

HRID 919364Notes

Reaction equation

HRID 919364 reaction equation
[NH2:1][OH:2].CC1CCCO1.[Na+].[Cl-].[C:11](#[N:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[C:11](=[N:1][OH:2])([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 5234Sodium ChlorideHCID 73012-MethyltetrahydrofuranHCID 7505Benzonitrile2×

Product 1

HCID 69186N'-Hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Benzonitrile (50.0 g, 0.485 mol) was added to a 250 mL flask and heated to 70° C. with stirring. Deionized water (1.0 g) was added and the temperature was lined out at 70° C. Aqueous hydroxylamine (50%, 37.50 g, 34.8 ml, assay was 53.3%, 0.605 moles) was added via a syringe pump over 1.5 hours while maintaining the temperature at 70°±2° C. HPLC analysis indicated that the conversion of benzonitrile was >99% after about 2.5 hours of reaction time. The batch was heated for a total of 3.5 hours at 70° C., then was cooled to 60° C. The batch was transferred to a 500 mL flask with 2-methyltetrahydrofuran (208.98 g), followed by 20 wt % aqueous NaCl (40.0 g). The mixture was heated to 60° C., and the phases were separated at 60° C. to give a solution of benzamide oxime in 2-methyltetrahydrofuran (281.80 g) and aqueous waste (44.61 g). The 2-methyltetrahydrofuran solution assayed for 21.73 wt % benzamide oxime.

Workup

  1. customwas lined out at 70° C
  2. temperaturewhile maintaining the temperature at 70°±2° C
  3. customafter about 2.5 hours
  4. customof reaction time
  5. temperatureThe batch was heated for a total of 3.5 hours at 70° C.
  6. temperaturewas cooled to 60° C
  7. temperatureThe mixture was heated to 60° C.
  8. customthe phases were separated at 60° C.

Sources & evidence

ORD record
ord-281c11d2751b42ff82e2858286f20b74
Source dataset
uspto-grants-2016_03
Patent number
US09273037B2

Reaction notes

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