Pyridine → 3,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide

HRID 46289Notes

Reaction equation

HRID 46289 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:15]=[C:16]([S:21](Cl)(=[O:23])=[O:22])[CH:17]=[CH:18][C:19]=1[F:20]>C(Cl)Cl>[F:13][C:14]1[CH:15]=[C:16]([S:21]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:22])=[O:23])[CH:17]=[CH:18][C:19]=1[F:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 27369133,4-Difluorobenzene-1-sulfonyl chloride

Product 1

HCID 535139793,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a slurry of 2-aminothiazole (23.88 g, 0.2384 mol) in methylene chloride (150 mL) and pyridine (38.0 mL, 0.470 mol) was added dropwise a solution of 3,4-difluorobenzenesulphonyl chloride (25.0 g, 0.118 mol) in 10 mL of methylene chloride. After stirring for 48 hours the reaction was diluted with more dichloromethane and extracted with 1N HCl. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography to give 3,4-difluoro-N-(thiazol-2-yl)benzenesulfonamide as a white solid. LCMS Rt=1.24 minutes MS m/z 277 [MH]+

Workup

  1. extractionextracted with 1N HCl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b825268082ba4067a69655ff911ac4af
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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