Triethylamine → HCID 86086565, compound

HRID 899141Notes

Reaction equation

HRID 899141 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH:14][CH2:15][CH2:16][OH:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([N:14]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:15][CH2:16][O:17][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17826Ethanol, 2-(phenethylamino)-HCID 31297Methanesulfonyl chloride

Product 1

HCID 86086565HCID 86086565, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (4.3 g, 0.037 mol) was added dropwise at 0° C. to a well stirred solution of 2-phenethylamino-ethanol (2.5 g, 0.015 mol, from step (i) above) and triethylamine (4.6 g, 0.045 mol) in dry dichloromethane (50 ml). The reaction mixture was stirred at room temperature for 3 h and quenched with water. The reaction mixture was extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane as eluent to yield (3 g) of compound as a solid.

Workup

  1. customquenched with water
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-3bbdfa282bf14babbefc9ffed375c121
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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