Triethylamine → HCID 22323657, compound

HRID 411853Notes

Reaction equation

HRID 411853 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CC#N>[CH3:13][S:14]([CH:4]([OH:5])[CH2:3][CH2:2][Cl:1])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123133-Chloro-1-propanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 22323657HCID 22323657, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-1-propanol (283 g, 2.99 mol) and triethylamine (629 mL, 4.5 mol) in CH3CN (3500 mL) at 10° C. was added dropwise methanesulfonyl chloride (518 g, 4.52 mol). The resulting reaction mixture was stirred overnight at room temperature, filtered and concentrated in vacuo to an oil. The oil was dissolved in CH2Cl2 and purified by filtration through silica gel. The appropriate fractions were combined and concentrated in vacuo to give the title compound 335 g (65%). TLC (Rf: 0.3; 20% EtOAc/Hexane). 1H NMR (CDCl3) δ2.1 (m, 2H, CH2), 2.96 (s, 3H, CH3) 3.59 (t, 2H, CH2), 4.28 (t, 2H, CH2). 13C NMR (CDCl3) δ31.5 (CH2), 37.0 (CH3), 40.2 (CH2), 66.3 (CH2).

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo to an oil
  4. dissolutionThe oil was dissolved in CH2Cl2
  5. filtrationpurified by filtration through silica gel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c21ca883362f417089171217069bbec7
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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