Triethylamine → HCID 19108697, compound

HRID 327662Notes

Reaction equation

HRID 327662 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(#N)C>[S:1]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 76889Benzenebutanol

Product 1

HCID 19108697HCID 19108697, compoundYield 63%

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 12 with 17.7 g (0.118 mole) of 4-phenylbutanol, 46.4 g (0.459 mole) of triethylamine in 100 ml additional acetonitrile followed by using extracting, washing and concentration procedures of Example 12 through the first evaporation. The viscous residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A Prep Pak 500® silica. Eluting solvent used was methylene chloride at a flow rate of 200 ml/min). Fractions containing the title compound were combined and the solvent was evaporated under reduced pressure to give 19.3 g of colorless, viscous oil which solidified on standing. The solid was recrystallized from ethyl ether-petroleum ether (bp range 30°-60° C.) to give 16.9 g (63%) of title compound as white solid, mp 79°-81° C.

Workup

  1. extractionby using extracting
  2. washwashing
  3. concentrationconcentration procedures of Example 12
  4. customthrough the first evaporation
  5. customThe viscous residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A Prep Pak 500® silica
  6. additionFractions containing the title compound
  7. customthe solvent was evaporated under reduced pressure
  8. customto give 19.3 g of colorless, viscous oil which
  9. customThe solid was recrystallized from ethyl ether-petroleum ether (bp range 30°-60° C.)

Sources & evidence

ORD record
ord-4dc8ff2045644379ba7a299aa63ef795
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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