5-Fluoro-2-methylbenzenesulphonyl chloride → HCID 11625024, compound

HRID 490669Notes

Reaction equation

HRID 490669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:26])=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:21]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:22]([C:20]2[CH:21]=[C:16]([F:15])[CH:17]=[CH:18][C:19]=2[CH3:26])(=[O:23])=[O:24])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 20099815HCID 20099815, compound

Product 1

HCID 11625024HCID 11625024, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.2 g (0.98 mmol) of 5-(2-chloro-phenyl)-pyridin-2-ylamine and 0.23 g of 5-fluoro-2-methyl-benzenesulfonyl chloride (1.1 mmol) in pyridine (10 ml) was stirred at RT until completion of reaction according to HPLC analysis (48 h). After concentration in vacuo the residue was taken up in EtOAc, the solution washed with 1 N aqueous HCl, saturated brine then dried over sodium sulphate and concentrated in vacuo. The precipitate was collected by filtration and dried in a high vacuum to give 0.21 g (57%) of N-[5-(2-chloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide as an off-white crystalline solid. ISN mass spectrum, m/e: 375.2 (M−1 calculated for C18H14ClFN2O2S: 375).

Workup

  1. customaccording to HPLC analysis (48 h)
  2. concentrationAfter concentration in vacuo the residue
  3. washthe solution washed with 1 N aqueous HCl, saturated brine
  4. dry with materialthen dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. filtrationThe precipitate was collected by filtration
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-4fa92e0d9d934643871fb2e4f4b21349
Source dataset
uspto-grants-2009_05
Patent number
US07528159B2

Reaction notes

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