Ethyl orthoformate → HCID 371811, compound

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N+:11]([O-:13])=[O:12])[C:5]([NH2:10])=[N:6][C:7]=1[NH:8][NH2:9].[CH2:14](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:7]2[N:6]([CH:14]=[N:9][N:8]=2)[C:5]([NH2:10])=[C:4]([N+:11]([O-:13])=[O:12])[N:3]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 130629835-Chloro-6-hydrazinyl-3-nitropyrazin-2-amine

Product 1

HCID 371811HCID 371811, compoundYield 77%

Procedure

To 5.0 g (0.024 mole) 5-chloro-6-hydrazino-3-nitropyrazinamine was added 50 ml of triethylorthoformate and the resulting suspension was heated at 100° for 1 hour. The reaction mixture was cooled, filtered and the dark brown solid washed with chloroform to give 3.9 g (77%) of 8-chloro-6-nitro-1,2,4-triazolo[4,3-a]pyrazine-5-amine as a brown solid, m.p. 220°, H' nmr (DMSO-d6): 9.65 (2H, broad singlet), 9.95 (1H, singlet); ms:m/e 214.

Workup

temperaturethe resulting suspension was heated at 100° for 1 hour
temperatureThe reaction mixture was cooled
filtrationfiltered
washthe dark brown solid washed with chloroform

Sources & evidence

ORD record: ord-74eebef57c284960a7468297e663b8fa
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04438266

Reaction notes

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