Ethanolamine → 3-(5-NITRO-1-METHYL-2-IMIDAZOLYL)-6-(beta-HYDROXYETHYL-AMINOMETHYLENEAMINO)-S-TRIAZOLO[4,3-b]PYRIDAZINE

HRID 435594Notes

Reaction equation

[N+](C1N(C)C(C2N3N=C(N=C[O:21][CH2:22][CH3:23])C=CC3=NN=2)=NC=1)([O-])=O.C(CN)O.[N+:28]([C:31]1[N:35]([CH3:36])[C:34]([C:37]2[N:41]3[N:42]=[C:43]([N:46]=[CH:47][NH:48]CCO)[CH:44]=[CH:45][C:40]3=[N:39][N:38]=2)=[N:33][CH:32]=1)([O-:30])=[O:29]>C(O)(C)C.O1CCOCC1>[N+:28]([C:31]1[N:35]([CH3:36])[C:34]([C:37]2[N:41]3[N:42]=[C:43]([N:46]=[C:47]([CH2:23][CH2:22][OH:21])[NH2:48])[CH:44]=[CH:45][C:40]3=[N:39][N:38]=2)=[N:33][CH:32]=1)([O-:30])=[O:29]

Participants

Conditions

Temperature: 20 °C

Procedure

1.2 g. crude 3-(5-nitro-1-methyl-2-imidazolyl)-6 -ethoxymethyleneamino-s-triazolo[4,3-b]pyridazine was dissolved in 13 ml. isopropanol-dioxan mixture (7:3), 1 ml. ethanolamine was added thereto at 20° C., while stirring, and stirring was then continued for 30 minutes. The precipitated crystals were filtered off with suction, washed with isopropanol and water and dried for 2 hours at 120° C. in a vacuum. There was obtained 1.07 g. of the desired 3-(5-nitro-1-methyl-2-imidazolyl)-6 -(β-hydroxyethylaminomethyleneamino)-s-triazolo[4,3-b]pyridazine, which has a melting point of 191° - 192° C.

Workup

stirringstirring
filtrationThe precipitated crystals were filtered off with suction
washwashed with isopropanol and water
customdried for 2 hours at 120° C. in a vacuum
customThere was obtained 1.07 g

Sources & evidence

ORD record: ord-6930a304c88640988faed0000fd17b28
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04006141

Reaction notes

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