Pyridine → 2,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide

HRID 46290

Reaction equation

HRID 46290 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[S:21]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 27342732,4-Difluorobenzenesulfonyl Chloride

Product 1

HCID 250389042,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 2-aminothiazole (15.08 g, 0.1506 mol) in methylene chloride (100 mL) and pyridine (24 mL, 0.30 mol) was added dropwise over 20 minutes a solution of 2,4-difluorobenzenesulfonyl chloride (10 mL, 0.07 mol) in 10 mL of methylene chloride. After stirring at room temperature for 48 hours the reaction was concentrated and purified by flash column chromatography eluting with hexane/ethyl acetate. LCMS Rt=1.21 minutes MS m/z 277 [MH]+

Workup

  1. concentrationwas concentrated
  2. custompurified by flash column chromatography
  3. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-b083043d358544dcbd3734bbd645a5dc
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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