Isopropanol → Diethylamine

HRID 435592Notes

Reaction equation

HRID 435592 reaction equation
[N+]([C:4]1N(C)[C:7]([C:10]2N3N=C(N)C=CC3=NN=2)=[N:6][CH:5]=1)([O-])=[O:2].[N+](C1N(C)C(C2N3N=C(N=C[O:40][CH2:41]C)C=CC3=NN=2)=NC=1)([O-])=O.[CH:43]([OH:46])(C)[CH3:44]>O1CCOCC1>[CH:41]([O-:40])([O-:2])[O:46][CH2:43][CH3:44].[CH2:5]([NH:6][CH2:7][CH3:10])[CH3:4]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 214559113-(5-Nitro-1-methyl-2-imidazolyl)-6-ethoxymethyleneamino-s-triazolo[4,3-b]pyridazineHCID 214559243-(5-Nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine

Product 2

HCID 8021DiethylamineHCID 53630039Ethylorthoformate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a manner analogous to that described in Example 13, from 1 g. 3-(5-nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[ 4,3-b]pyridazine and 10 ml. ethyl orthoformate, there was prepared crude 3-(5-nitro-1-methyl-2-imidazolyl)-6-ethoxymethyleneamino-s-triazolo[4,3-b]pyridazine which, with 13 ml. of a solvent mixture of isopropanol and dioxan (7:3) and 1.1 ml. diethylamine gave, after a reaction time of 30 minutes at 20° C., subsequent evaporation of the solution in a vacuum at a bath temperature of 80° C., trituration of the residue with a little isopropanol and water and drying for 2 hours at 120° C. in a vaccum, 0.84 g. of the desired 3-(5-nitro-1-methyl-2-imidazolyl)-6-(diethylaminomethyleneamino)-s-triazolo[4,3-b]pyridazine which has a melting point of 155° - 156° C.

Sources & evidence

ORD record
ord-5f87b6e3421542a7aad13ea0e1205a11
Source dataset
uspto-grants-1977_02
Patent number
US04006141

Reaction notes

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