Ethylene Glycol → HCID 20368970, compound

HRID 616730Notes

Reaction equation

HRID 616730 reaction equation
[H-].[Na+].C(O)CO.[S:7](Cl)(=[O:10])(=[O:9])[NH2:8].S(O[CH2:17][CH2:18][O:19][S:20](=[O:23])(=[O:22])[NH2:21])(=O)(=O)N.[CH2:24]([OH:30])[CH2:25][CH2:26]CCO>COCCOC>[S:7]([O:30][CH2:24][CH2:25][CH2:26][CH2:17][CH2:18][O:19][S:20](=[O:22])(=[O:23])[NH2:21])(=[O:10])(=[O:9])[NH2:8]

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 81051,5-PentanediolHCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 148884Sulfamic acid, ethylene ester

Product 1

HCID 20368970HCID 20368970, 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. Sulfamoyl chloride (20.79 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 6.1 g. (58%) of 1,2-bis-O-sulfamyl-1,2-ethanediol, m.p. 96.5°-99° C. When in the above procedure 1,5-pentanediol is employed in place of ethylene glycol, 1,5-bis-O-sulfamyl-1,5-pentanediol is obtained.

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
  10. customto yield 6.1 g

Sources & evidence

ORD record
ord-aaa72c25d3ab4784838df9c131a64385
Source dataset
uspto-grants-1978_02
Patent number
US04075351

Reaction notes

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