Water → HCID 54566916, compound

HRID 1613827Notes

Reaction equation

HRID 1613827 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].OCCO[CH2:13][CH2:14][OH:15].[S:16](Cl)(=[O:19])(=[O:18])[NH2:17].C(N([CH2:26][CH3:27])CC)C.[OH2:28]>C(#N)C.C(OCC)(=O)C>[NH2:17][S:16]([O:19][CH2:26][CH2:27][O:2][C:1]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[O:5][CH2:13][CH2:14][O:15][S:16](=[O:19])(=[O:18])[NH2:17])(=[O:28])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 21114759HCID 21114759, compound

Product 1

HCID 54566916HCID 54566916, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 25.0 g (0.13 mole) of resorcinol-bis(β-hydroxyethyl)ether (Lancaster Synthesis, Windham, NH 03087) in 150 ml of acetonitrile was added simultaneously 170 ml (0.53 mole) of sulfamoyl chloride solution (3.14M solution in acetonitrile) and 54.1 g (0.54 mole) of triethylamine (temperature ≤15° C.) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was treated with 200 ml of water and 300 ml of ethyl acetate, the layers were separated, and the organic layer was washed with two 200 ml portions of water. The organic solvents were evaporated under reduced pressure and the solid residue was treated with 500 ml of ethyl acetate and 200 ml of water. The mixture was filtered1 and the filtrate layers were separated. The organic layer was washed with five 200 ml portions of water (filtrate pH neutral to pH paper) and dried (magnesium sulfate). The solvent was evaporated under reduced pressure and the solid residue was dissolved in 300 ml of ethyl acetate and filtered through celite. The filtrate was evaporated under reduced pressure and the solid residue was recrystallized from ethyl acetate to yield 19.6 g (44%) of an off-white solid, mp 147°-149° C.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with two 200 ml portions of water
  3. customThe organic solvents were evaporated under reduced pressure
  4. additionthe solid residue was treated with 500 ml of ethyl acetate and 200 ml of water
  5. customthe filtrate layers were separated
  6. washThe organic layer was washed with five 200 ml portions of water (filtrate pH neutral to pH paper)
  7. dry with materialdried (magnesium sulfate)
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionthe solid residue was dissolved in 300 ml of ethyl acetate
  10. filtrationfiltered through celite
  11. customThe filtrate was evaporated under reduced pressure
  12. customthe solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-230b38eb1e2649ae8e77ca0790f8e5b7
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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