Chlorosulfonic acid → 2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

HRID 411606Notes

Reaction equation

HRID 411606 reaction equation
Cl.[O:2]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:19][S:20](O)(=[O:22])=[O:21]>ClCCl>[Cl:19][S:20]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:11])=[CH:4][CH:5]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 699610482-(phenoxyacetyl)aminopyridine HCl salt

Product 1

HCID 185412102-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.32 g of 2-(phenoxyacetyl)aminopyridine HCl salt (5 mmole) was resuspended in 10 ml of dichloromethane and 2 ml of chlorosulfonic acid was added in ice-bath to give clear solution. The solution was stirred at room temperature for 3 hr. The reaction mixture was added to ice-water with good stirring to give white solids. The solids were filtered, washed with acetonitrile, and dried in vacuo. 0.65 g of solid was obtained. M. P. 170-175° C. (decomposition)

Workup

  1. customto give clear solution
  2. stirringwith good stirring
  3. customto give white solids
  4. filtrationThe solids were filtered
  5. washwashed with acetonitrile
  6. customdried in vacuo

Sources & evidence

ORD record
ord-64695ade29fe4717bc3cd6a11727b798
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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