2-(2-Aminoethoxy)pyridine → N-(2-(pyridin-2-yloxy)ethyl)thioacetamide

HRID 2224750Notes

Reaction equation

HRID 2224750 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][NH2:10].[C:11](N1C(=O)C2C(=CC=CC=2)C1=O)(=[S:13])[CH3:12]>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][NH:10][C:11](=[S:13])[CH3:12]

Participants

4

Reactant 2

HCID 968902-(2-Aminoethoxy)pyridineHCID 451186352-Ethanethioylisoindoline-1,3-dione

Product 1

HCID 45116268N-(2-(pyridin-2-yloxy)ethyl)thioacetamideYield 49.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Add 2-(pyridin-2-yloxy)ethylamine (500 mg, 3.62 mmol) to a solution of 2-thioacetyl-isoindole-1,3-dione (743 mg, 3.62 mmol) in CHCl3 (18 mL) at 0° C. After stirring for 15 minutes, concentrate the solution, redissolve in ethyl acetate (25 mL), filter, and concentrate again. Flash chromatography (SiO2, 1:1 EtOAc/Hex) gives N-(2-(pyridin-2-yloxy)ethyl)thioacetamide (350 mg, 49%) as a beige/pink solid. 1H NMR (CDCl3) δ 8.79 (br s, 1H), 8.10-8.08 (m, 1H), 7.58-7.65 (m, 1H), 6.92-7.00 (m, 1H), 6.76-6.82 (m, 1H), 4.57-4.65 (m, 2H), 3.98-4.05 (m, 2H), 2.56 (s, 3H).

Workup

  1. concentrationconcentrate the solution
  2. dissolutionredissolve in ethyl acetate (25 mL)
  3. filtrationfilter
  4. concentrationconcentrate again

Sources & evidence

ORD record
ord-0ed338e826764e78b8e88a039dd387cb
Source dataset
uspto-grants-2008_05
Patent number
US07378447B2

Reaction notes

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