Pyridine → HCID 57585043, compound

HRID 2077500Notes

Reaction equation

HRID 2077500 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 57585043HCID 57585043, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

6-Chloropyridin-2-amine (0.3 g, 2 mmol) was dissolved in DCM (20 mL) and then pyridine (0.57 mL, 7.0 mmol) was added to the mixture with stirring. Then, benzenesulfonyl chloride (0.36 mL, 2.8 mmol) was added into the mixture. The mixture was allowed to stir under inert atmosphere for 2 hours. The mixture was diluted with DCM and saturated NaHCO3, and then the aqueous layer was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (10-100% EtOAc/hexanes) to provide N-(6-chloropyridin-2-yl)benzenesulfonamide (0.5 g, 80% yield) as a colorless oil. MS (ESI pos. ion) m/z: 254 (MH+). Calculated exact mass for C11H8ClNO2S: 253.

Workup

  1. stirringto stir under inert atmosphere for 2 hours
  2. extractionthe aqueous layer was extracted with DCM three times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography (10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-05fb5e6c767b4b2594bb4def7ff6e95f
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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