2-Aminothiazole → 6-chloro-N-(1,3-thiazol-2-yl)pyridine-3-sulfonamide

HRID 1670582Notes

Reaction equation

HRID 1670582 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 9431916-chloro-N-(1,3-thiazol-2-yl)pyridine-3-sulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under a N2 atmosphere, a mixture of the 6-chloropyridine-3-sulfonyl chloride (0.95 gm, 4.51 mmol), 2-aminothiazole (0.452 gm, 4.51 mmol), and pyridine (7.0 mL) was stirred at RT for 19 h. The crude product was purified via silica gel chromatography using (2-10%) MeOH in CH2Cl2. After evaporating the solvents under reduced pressure, purification via silica gel chromatography using 2-10% MeOH in CH2Cl2 gave 6-chloro-N-(thiazol-2-yl)pyridine-3-sulfonamide as a white solid (0.841 g, 68%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=276.2; tR=0.6 min.

Workup

  1. customThe crude product was purified via silica gel chromatography
  2. customAfter evaporating the solvents
  3. customunder reduced pressure, purification via silica gel chromatography

Sources & evidence

ORD record
ord-e231b41d9e584fb7abecb3ebd76f4a17
Source dataset
uspto-grants-2011_08
Patent number
US07994174B2

Reaction notes

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