Triethylamine → HCID 22323657, compound

HRID 495873Notes

Reaction equation

HRID 495873 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) δ 2.1 (m, 2H, CH2), 2.96 (s, 3H, CH3), 3.59 (t, 2H, CH2), 4.28 (t, 2H, CH2). 13C NMR (CDCl3) δ 31.5 (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-5bc32511b3c542129c67e68da8636ac1
Source dataset
uspto-grants-2005_09
Patent number
US06942966B1

Reaction notes

Loading…