Methanol → N'-Hydroxybenzenecarboximidamide

HRID 578886Notes

Reaction equation

HRID 578886 reaction equation
Cl.[NH2:2][OH:3].CO.[OH-].[Na+].[C:8](#[N:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8](=[N:2][OH:3])([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 7505Benzonitrile2×HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 69186N'-Hydroxybenzenecarboximidamide

Conditions

Temperature
57.5 °C

Procedure

Hydroxylamine hydrochloride (8.85 g, 0.126 moles) and methanol (45 mL) were charged to a 100 mL flask, followed by 51% sodium hydroxide (9.82 g, 0.125 moles). To this mixture was added benzonitrile (10.32 g, 0.100 moles), and the reaction was heated to 55-60° C. and held for 2 hours. HPLC showed that the reaction was complete by the disappearance of benzonitrile. A portion of the methanol (30 mL) was removed by distillation, deionized (DI) water was added (22 mL), and the remaining methanol was distilled at 300 torr to give two liquid phases (benzamide oxime melt and salt water). 2-Methyltetrahydrofuran (20.0 g) was added, and the aqueous salt phase was drained off to give 33.34 g of a solution of benzamide oxime in 2-methyltetrahydrofuran, 39.45% by loss on drying and HPLC. The yield of benzamide oxime was 96.5%.

Workup

  1. customA portion of the methanol (30 mL) was removed by distillation
  2. additionwas added (22 mL)
  3. distillationthe remaining methanol was distilled at 300 torr

Sources & evidence

ORD record
ord-8c1b639cac754abea89d1644ea88e862
Source dataset
uspto-grants-2015_05
Patent number
US09040711B2

Reaction notes

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