Ammonia → N,N-diallyl-4-aminopyridine-3-sulfonamide

HRID 2283345Notes

Reaction equation

HRID 2283345 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1Cl)(=[O:7])=[O:6])[CH:2]=[CH2:3].[I-].[Li+].[NH3:20]>>[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH2:20])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 66321Lithium iodideHCID 57750928N,N-diallyl-4-chloropyridine-3-sulfonamide

Product 1

HCID 57750998N,N-diallyl-4-aminopyridine-3-sulfonamideYield 59%

Conditions

Temperature
120 °C

Procedure

A mixture of N,N-diallyl-4-chloropyridine-3-sulfonamide (1.5 g, 5.5 mmol), lithium iodide (0.74 g, 5.5 mmol) and ammonia (7 M in methanol, 14 mL, 5.5 mmol) under an atmosphere of argon was heated at 120° C. for 2 h in a microwave reactor. Silica was added and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (95:5) as the eluent, gave the title compound in 59% yield.

Workup

  1. additionSilica was added
  2. customthe solvent was evaporated
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-e073639fe2e344d79c611e80ecf47c27
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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