Hydrazine hydrate (1:1) → N-[1-(5-Oxo-3-phenyl-4,5-dihydro-1,2,4-triazin-6-yl)ethyl]acetamide

HRID 57673

Reaction equation

Cl.[C:2]1([C:8](=[NH:10])[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:12]N.[C:14]([NH:17][CH:18]([CH3:26])[C:19](=O)[C:20](OCC)=[O:21])(=[O:16])[CH3:15]>C(O)C>[O:21]=[C:20]1[C:19]([CH:18]([NH:17][C:14](=[O:16])[CH3:15])[CH3:26])=[N:12][N:9]=[C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:10]1

Participants

Conditions

Temperature: 45 °C

Procedure

48 g (306 mmol) of benzenecarboximidamide hydrochloride were dissolved in 1.2 l ethanol, and 16.4 ml (337 mmol) of hydrazine hydrate were added. The mixture was stirred at 45° C. for 3 h. 86 g (459 mmol) of ethyl 3-acetamido-2-oxobutanoate (Example 13A), dissolved in 600 ml of ethanol, were added dropwise. The mixture was stirred at 80° C. for another 6 h and at RT for another 12 h. The reaction mixture was chromatographed on silica gel (mobile phase dichloromethane/methanol 20:1). This gave 23.2 g (26% of theory) of the product as a solid.

Workup

additionwere added dropwise
stirringThe mixture was stirred at 80° C. for another 6 h and at RT for another 12 h
customThe reaction mixture was chromatographed on silica gel (mobile phase dichloromethane/methanol 20:1)

Sources & evidence

ORD record: ord-118692bcb7994c11966300e0473ecc00
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434731B2

Linked notes

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