Ammonium Hydroxide → 6-Cyanopyridine-3-sulfonamide

HRID 331185Notes

Reaction equation

HRID 331185 reaction equation
[OH-].[NH4+:2].[C:3]([C:5]1[N:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4]>>[C:3]([C:5]1[N:10]=[CH:9][C:8]([S:11]([NH2:2])(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 470031906-Cyanopyridine-3-sulfonyl chloride

Product 1

HCID 576254346-Cyanopyridine-3-sulfonamideYield 80%

Conditions

Temperature
2.5 °C

Procedure

To an ice-cold solution of ammonium hydroxide (75 ml, 25% w/v) is added 6-cyanopyridine-3-sulfonyl chloride (12.5 g) portionwise and the mixture is stirred for 30 minutes at 0-5° C. The reaction mixture is then concentrated to ⅕th of its original volume and cooled. The precipitate is filtered and dried under vacuum to afford the title compound as light brown solid (9 g, Yield 80%). 1H NMR (DMSO-d6:400 MHz) δ 9.10 (1H, s), 8.33-8.35 (1H, m), 8.23-8.25(1H, d); 7.88-8.03 (2H, bs); HPLC (max plot) 98%, Rt 4.67 min; LC/MS: (ES+) 183.8.

Workup

  1. concentrationThe reaction mixture is then concentrated to ⅕th of its original volume
  2. temperaturecooled
  3. filtrationThe precipitate is filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a669b74c4b5b413eb0b824f41a8dade8
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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