1-Propanesulfonyl chloride → HCID 22176567, compound

HRID 1797192Notes

Reaction equation

HRID 1797192 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2]C.[OH:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])[CH2:10][NH2:11].[CH2:22]1CCN2C(=NCCC2)CC1>C(Cl)Cl>[OH:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])[CH2:10][NH:11][S:4]([CH:1]([CH3:2])[CH3:22])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22176538HCID 22176538, compound

Product 1

HCID 22176567HCID 22176567, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 500 mL, 3 neck flask fitted with a stirrer and thermometer, 2.98 g. of propanesulfonyl chloride was added dropwise to 3.92 g. of 2-hydroxy-2-(4-nitrophenyl)propylamine and 3.19 g. of DBU in CH2Cl2 (200 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred overnight at this temperature. In the morning, reaction was diluted with CH2Cl2 (100 mL) and the organic layer was washed two times with H2O, dried over Na2SO4, and concentrated under reduced vacuum to yield a viscous oil. This material was purified via silica gel chromatography employing the Water's Prep 2000 and eluting with a solvent of hexane/ethyl acetate 1:1 to yield the intermediate title compound (940 mg, 16%) as a viscous oil. Ion spray M.S. 302.1 (M*−1).

Workup

  1. customIn a 500 mL, 3 neck flask fitted with a stirrer
  2. customIn the morning, reaction
  3. washthe organic layer was washed two times with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced vacuum
  6. customto yield a viscous oil
  7. customThis material was purified via silica gel chromatography
  8. washeluting with a solvent of hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-e65eeed6269842008f375406af99c4c0
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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