Ethanesulfonyl chloride → HCID 49818816, compound

HRID 391346Notes

Reaction equation

HRID 391346 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH2:17])[CH:12]=[N:13][CH:14]=1.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19]>N1C=CC=CC=1.CCOC(C)=O.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH:12]=[N:13][CH:14]=1

Participants

6

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 59578385HCID 59578385, compound

Product 1

HCID 49818816HCID 49818816, compoundYield 17.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)ethanamine (35 mg, 0.131 mmol) in pyridine (3 ml) at 0° C. was added ethanesulfonyl chloride (0.037 ml, 0.393 mmol) and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and water, extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification via PTLC (eluent; 60% EtOAc/Heptane, v/v) gave N-(2-(5-(2,3-dichlorophenyl)pyridin-3-yl)ethyl)ethanesulfonamide (8.1 mg, 0.023 mmol, 17% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification via PTLC (eluent; 60% EtOAc/Heptane, v/v)

Sources & evidence

ORD record
ord-e2241f5b24d44e56a1f78d021e551c7d
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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