Methanol → N'-Hydroxybenzenecarboximidamide

Temperature

68 °C

Hydroxylamine hydrochloride (88.5 g, 1.26 moles) and methanol (450 mL) were charged to a 1000 mL flask, followed by 51% sodium hydroxide (97.7 g, 1.25 moles). Benzonitrile (103.1 g, 1.00 moles) was added and the reaction was heated to 65-71° C. for 4 hours. HPLC showed that the reaction was complete by the disappearance of benzonitrile. A portion of the methanol (366 mL) was removed by distillation, DI water was added (200 mL), and the remaining methanol was distilled at 200 torr to give two liquid phases (benzamide oxime melt and salt water). Butyl acetate (650 mL) and DI water (100 mL) were added, and the aqueous salt phase was drained off. The butyl acetate solution was washed once with 100 mL of water to give 715.04 g of a blue-tinted cloudy solution of benzamide oxime in butyl acetate, 18.1% by loss on drying. Yield of benzamide oxime was 95.1% with a 3.4% yield of benzamide by-product.

1. customA portion of the methanol (366 mL) was removed by distillation, DI water
2. additionwas added (200 mL)
3. distillationthe remaining methanol was distilled at 200 torr

ORD record

ord-ecae867646cb4e50baf8fc57aa4b3749

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273037B2