N,N-Dimethylaniline → chlorobenzotriazine N-oxide

HRID 1020725Notes

Reaction equation

HRID 1020725 reaction equation
O[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N+:5]([O-:12])=[N:4][N:3]=1.P(Cl)(Cl)([Cl:15])=O.CN(C)C1C=CC=CC=1>>[Cl:15][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N+:5]([O-:12])=[N:4][N:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178526300HCID 178526300, compound

Product 1

HCID 86663331chlorobenzotriazine N-oxide

Procedure

The amino-benzotriazine N-oxide (16) is diazotized with NaNO2/HCl and the intermediate diazonium salt (not shown) is hydrolysed to form the hydroxybenzotriazine N-oxide compound (17). Reaction of the hydroxybenzotriazine N-oxide compound (17) with phosphorus oxychloride in the presence of a non-interfering base such as N,N-dimethylaniline gives the chlorobenzotriazine N-oxide compound (18). The chlorination reaction is typically carried out with heating, for example at reflux temperatures.

Sources & evidence

ORD record
ord-cd89b64bb0a0437c89cd117b10c6d559
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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