Triethylamine → HCID 22323657, compound

HRID 1533462Notes

Reaction equation

HRID 1533462 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-b8bddb0f2f2b44699c0b0b1879d7a5c9
Source dataset
uspto-grants-2001_03
Patent number
US06207826B1

Reaction notes

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