Dibenzylamine → 2-chloropyridine-3-sulfonamide

HRID 2109919Notes

Reaction equation

HRID 2109919 reaction equation
[Cl:1][C:2]1[C:7](N)=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1([S:16](Cl)(=[O:18])=[O:17])C=CC=CN1.[N:20]([O-])=O.[Na+].S(Cl)(Cl)(=O)=O.C(NCC1C=CC=CC=1)C1C=CC=CC=1>>[Cl:1][C:2]1[C:7]([S:16]([NH2:20])(=[O:18])=[O:17])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 5

HCID 7656DibenzylamineHCID 24648Sulfuryl chlorideHCID 805282-Chloro-3-pyridylamineHCID 23668193Sodium NitriteHCID 86600442HCID 86600442, compound

Product 1

HCID 122344452-chloropyridine-3-sulfonamide

Procedure

The synthesis of a 2-halopyridine sulfonamide intermediate is illustrated in Reaction Scheme L. The 2-chloro-3-aminopyridine is converted to the 2-chloropyridinesulfonyl chloride by reaction with sodium nitrite/acid and sulfuryl chloride. This compound is then allowed to react with dibenzylamine to provide the desired 2-chloropyridine 3-sulfonamide intermediate. This compound may then be carried on to a final product using the methods described in Reaction Schemes A and D.

Workup

  1. customis illustrated in Reaction Scheme L

Sources & evidence

ORD record
ord-44ebb87170a341cc8dc4910d1a478b69
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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