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

HRID 1644659Notes

Reaction equation

HRID 1644659 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][N:15]=1>>[Cl:13][C:14]1[N:15]=[CH:16][C:17]([S:20]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 9431916-chloro-N-(1,3-thiazol-2-yl)pyridine-3-sulfonamide

Procedure

To 2-AMINOTHIAZOLE (1.80 g, 0.0179 mol) in Pyridine (6 mL, 0.08 mol) at 0° C. was added 2-Chloropyridine-5-sulfonyl chloride (1.55 g, 0.00717 mol) portion-wise. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate (150 mL), washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified on ISCO companion (silica gel, 10% to 100% ethyl acetate in hexanes) to give product as a brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate (150 mL)
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on ISCO companion (silica gel, 10% to 100% ethyl acetate in hexanes)
  8. customto give product as a brown solid

Sources & evidence

ORD record
ord-51ae072adf82447784a6626399167d5d
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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