Ammonium Hydroxide → 6-amino-N-(thiazol-2-yl)pyridine-3-sulfonamide

HRID 1670583Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:18]>C(O)C>[NH2:18][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Under a N2 atmosphere, a mixture of 6-chloro-N-(thiazol-2-yl)pyridine-3-sulfonamide (0.7 g, 2.54 mmol), ammonium hydroxide (7.5 mL) and ethanol (7.5 mL), was stirred at 120° C. in a sealed tube for 4 days. The reaction was cooled to RT. After evaporating the solvents under reduced pressure, purification via silica gel chromatography using 5%-10% methanol in CH2Cl2 gave 6-amino-N-(thiazol-2-yl)pyridine-3-sulfonamide as a orange solid (0.14 g, 22%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=257.2; tR=0.2 min.

Workup

temperatureThe reaction was cooled to RT
customAfter evaporating the solvents
customunder reduced pressure, purification via silica gel chromatography

Sources & evidence

ORD record: ord-64ae8275d387401298de2a6024ab768d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994174B2

Reaction notes

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