Triethylamine → Hepsulfam

HRID 1613365Notes

Reaction equation

HRID 1613365 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[CH2:6]([OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].C(N(CC)CC)C>C(#N)C>[CH2:9]([CH2:8][CH2:7][CH2:6][O:14][S:1]([NH2:2])(=[O:4])=[O:3])[CH2:10][CH2:11][CH2:12][O:13][S:1]([NH2:2])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123811,7-HeptanediolHCID 24499Chlorosulfamic acid

Product 1

HCID 100606HepsulfamYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The title compound was obtained using the following procedure: The sulfamoyl chloride in acetonitrile solution prepared in (a) was reacted as in Example 11 with 10.5 g (0.0755 mole) of 1,7-heptanediol (95%), 30.3 g (0.300 mole) of triethylamine in 100 ml additional acetonitrile followed by using extracting, washing and concentration procedures of Example 11 through the first evaporation. The viscous residue which solidified on standing was purified by high pressure liquid chromatography using the Waters Associates® Prep LC/System 500A with PrepPAK® 500 silica. Eluting solvent used was 10:1 mixture methylene chloride-acetone at a flow rate of 200 ml/min. Fractions containing the title compound were combined and the solvents were evaporated under reduced pressure to give a viscous oil which solidified on standing. The solid was recrystallized from wet methylene chloride to give 8.2 g (37% yield) of title compound as white solid, mp 88.5°-90.5° C.

Workup

  1. extractionby using extracting
  2. washwashing
  3. concentrationconcentration procedures of Example 11
  4. customthrough the first evaporation
  5. customwas purified by high pressure liquid chromatography
  6. additionFractions containing the title compound
  7. customthe solvents were evaporated under reduced pressure
  8. customto give a viscous oil which
  9. customThe solid was recrystallized from wet methylene chloride

Sources & evidence

ORD record
ord-a8542fe0b7b94f00ad7b9bc689411af3
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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