Hydrazine hydrate (1:1) → N-{1-[3-(3-Nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

HRID 1270298Notes

Reaction equation

O.[NH2:2]N.Cl.[N+:5]([C:8]1[CH:9]=[C:10]([C:14](=[NH:16])[NH2:15])[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6].[C:17]([NH:20][CH:21]([CH3:29])[C:22](=O)[C:23](OCC)=[O:24])(=[O:19])[CH3:18]>C(O)C>[N+:5]([C:8]1[CH:9]=[C:10]([C:14]2[NH:15][C:23](=[O:24])[C:22]([CH:21]([NH:20][C:17](=[O:19])[CH3:18])[CH3:29])=[N:2][N:16]=2)[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

Conditions

Temperature: 20 °C

Procedure

2.89 g (2.81 ml, 57.73 mmol) of hydrazine hydrate are added dropwise to 9.70 g (48.11 mmol) of 3-nitrobenzenecarboximidamide hydrochloride from example 2A in 200 ml of ethanol. The mixture is stirred for one hour at 20° C. After this time, 13.51 g (72.17 mmol) of ethyl 3-(acetylamino)-2-oxobutanoate from example 4A are added in ethanol, and the reaction mixture is stirred for 4 h at a bath temperature of 70–80° C., subsequently for 12 h at 20° C. The mixture is concentrated and the residue is purified by flash chromatography (eluent: ethyl acetate, subsequently dichloromethane/methanol 30:1).

Workup

stirringthe reaction mixture is stirred for 4 h at a bath temperature of 70–80° C.
waitsubsequently for 12 h at 20° C
concentrationThe mixture is concentrated
customthe residue is purified by flash chromatography (eluent

Sources & evidence

ORD record: ord-954d6de5d8b543e19804ac13c792644e
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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