Sodium Hydroxide → Sodium Azide

HRID 460165Notes

Reaction equation

HRID 460165 reaction equation
N1C=CC(C2SC=C(C([N:14]=[N+:15]=[N-:16])=O)N=2)=CC=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](C2SC=C(C(O)=O)N=2)[CH:18]=1.[OH-].[Na+:32].C(Cl)(=O)C(Cl)=O>O>[N-:14]=[N+:15]=[N-:16].[Na+:32].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:14]=[N+:15]=[N-:16])[CH:18]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 187717402-(4-Pyridinyl)-4-thiazolylcarbonylazide

Product 2

HCID 33557Sodium AzideHCID 120666873-Azidopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner similar to that described for the preparation of 2-(4-pyridinyl)-4-thiazolylcarbonylazide, 6.0 g of 2-(3-pyridinyl)-4-thiazolylcarboxylic acid was treated successively with NaOH, oxalyl chloride and a solution of NaN3 in water to give the 3-pyridinylazide as a pale brown solid. MS m/z: 204.5 (M−N2+H).

Sources & evidence

ORD record
ord-71f97e4564f9488fb60f42ca14a3b848
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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