Pyridine → 2-(4-Chlorophenoxy)ethanol sulfamate

HRID 1613764Notes

Reaction equation

HRID 1613764 reaction equation
C[NH:2][S:3](Cl)(=[O:5])=[O:4].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[S:3]([O:15][CH2:14][CH2:13][O:12][C:11]1[CH:16]=[CH:17][C:8]([Cl:7])=[CH:9][CH:10]=1)(=[O:5])(=[O:4])[NH2:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 159072-(4-Chlorophenoxy)ethanolHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 191086672-(4-Chlorophenoxy)ethanol sulfamateYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 45.0 g (0.347 mole) of methylsulfamoyl chloride prepared above in 100 ml of methylene chloride was added in a thin stream a solution of 25.0 g (0.145 mole) of 2-(4-chlorophenoxy)ethanol (Lancaster Synthesis, Inc., Windham, N.H. 03087) in 30 ml (0.369 mole) of pyridine and 100 ml of methylene chloride and the reaction mixture was stirred at ambient temperature for 3 days. The solids were removed by filtration and the filtrate was evaporated under reduced pressure to yield a brown viscous residue. The residue was partitioned between water and ethyl ether (400 ml each). The organic layer was washed twice with 300 ml portions of water, dried over magnesium sulfate (MgSO4) and the solvent evaporated under reduced pressure to yield a solid residue. The solid was triturated with 100 ml of isopropyl ether and the solid was recollected by filtration. The solid was recrystallized from isopropyl ether to give 12.9 g (34%) of title compound as a white solid, m.p. 101°-104° C.

Workup

  1. customThe solids were removed by filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customto yield a brown viscous residue
  4. customThe residue was partitioned between water and ethyl ether (400 ml each)
  5. washThe organic layer was washed twice with 300 ml portions of water
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. customthe solvent evaporated under reduced pressure
  8. customto yield a solid residue
  9. customThe solid was triturated with 100 ml of isopropyl ether
  10. filtrationthe solid was recollected by filtration
  11. customThe solid was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-61e32017b0714e0fb769286aca977fcd
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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