Ethylene Glycol → HCID 20368981, compound

HRID 1973473Notes

Reaction equation

HRID 1973473 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[CH3:7][N:8]([CH3:13])[S:9](Cl)(=[O:11])=[O:10]>COCCOC>[CH3:7][N:8]([CH3:13])[S:9]([O:5][CH2:4][CH2:3][O:6][S:9](=[O:11])(=[O:10])[N:8]([CH3:13])[CH3:7])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 20368981HCID 20368981, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A 57% oil dispersion of sodium hydride (8.45 g.; 0.20 mol.) is added to a solution of ethylene glycol (3.1 g.; 0.05 mol.) in 1,2-dimethoxyethane (100 ml.). The resulting suspension is stirred at room temperature for 2 hours and then cooled to +4° C. N,N-dimethylsulfamoyl chloride, 25.8 g. (0.18 mol.), is dissolved in 1,2-dimethoxyethane (400 ml.) and added dropwise to the solution with stirring. The reaction mixture is stirred at +4° C for an additional 24 hours. A precipitate forms which is filtered off and the filtrate is concentrated. The residue is partitioned between heptane and methanol, and the methanol solution is concentrated to a syrup which crystallizes from ethyl acetate to yield 1,2-bis-O-(N,N-dimethylsulfamyl)-1,2-ethanediol.

Workup

  1. temperaturecooled to +4° C
  2. additionadded dropwise to the solution
  3. stirringwith stirring
  4. stirringThe reaction mixture is stirred at +4° C for an additional 24 hours
  5. filtrationA precipitate forms which is filtered off
  6. concentrationthe filtrate is concentrated
  7. customThe residue is partitioned between heptane and methanol
  8. concentrationthe methanol solution is concentrated to a syrup which
  9. customcrystallizes from ethyl acetate

Sources & evidence

ORD record
ord-189f37891da04fc5831eb1b26f262fd4
Source dataset
uspto-grants-1976_12
Patent number
US03997585

Reaction notes

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