Hydrochloric Acid → Azide

HRID 1679543Notes

Reaction equation

HRID 1679543 reaction equation
NN.[N:3]1[NH:4][C:5](=[O:14])[NH:6][C:7](=[O:13])[C:8]=1[C:9]([NH:11][NH2:12])=[O:10].Cl.[N:16]([O-])=[O:17].[Na+]>O.CN(C)C=O>[N-:16]=[N+:11]=[N-:12].[N:3]1[NH:4][C:5](=[O:14])[NH:6][C:7](=[O:13])[C:8]=1[C:9]([OH:17])=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 1317110581,2,4-Triazine-3,5-dione-6-carboxylic acid hydrazide hydrazine salt

Product 2

HCID 33558AzideHCID 50736533,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.01 g. (0.005 mole) of 1,2,4-triazine-3,5-dione-6-carboxylic acid hydrazide hydrazine salt in 50 ml. of water, 20 ml. of 1N hydrochloric acid and 70 ml. of N,N-dimethylformamide was cooled to -3° C. A solution of 0.83 g. (0.012 mole) of sodium nitrite in 4 ml. of water was added to the hydrazide solution and the mixture was stirred at -3° C. to -5° C. for 30 minutes to give in solution the acid azide of 1,2,4-triazine-3,5-dione-6-carboxylic acid.

Sources & evidence

ORD record
ord-3eb79b8e1a574c8a8ef528de851660b1
Source dataset
uspto-grants-1978_03
Patent number
US04081441

Reaction notes

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