3-Chloro-1,2-propanediol → 1-(2,3-Dihydroxypropyl)-3-ethylimidazolium Chloride

HRID 62548

Reaction equation

HRID 62548 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[CH3:2].[Cl:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12]>CO>[Cl-:8].[OH:13][CH:10]([CH2:11][OH:12])[CH2:9][N+:5]1[CH:6]=[CH:7][N:3]([CH2:1][CH3:2])[CH:4]=1

Participants

4

Reactant 2

HCID 72903-Chloro-1,2-propanediolHCID 815401-Ethyl-1H-imidazole

Product 1

HCID 866682651-(2,3-Dihydroxypropyl)-3-ethylimidazolium ChlorideYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Ethylimidazole (2.40 g, 25.0 mmol) and 3-chloro-1,2-propanediol (2.76 g, 25.0 mmol) were stirred in a 130° C. oil bath for 48 h, after which the flask was placed under vacuum and stirring continued at 130° C. for another 48 h. The residue was then dissolved in CH3OH, transferred to a tared flask and concentrated to afford the product as a viscous brown oil (4.88 g, 94%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 1.41 (t, J=7.24 Hz, 3H) 3.23 (dd, J=11.17, 6.96 Hz, 1H) 3.37-3.47 (m, 1H) 3.70-3.86 (m, 1H) 4.11 (dd, J=13.74, 7.69 Hz, 1H) 4.22 (q, J=7.33 Hz, 2H) 4.33 (dd, J=13.74, 3.11 Hz, 1H) 5.19 (br. s., 1H) 5.59 (br. s., 1H) 7.78 (t, J=1.74 Hz, 1H) 7.85 (t, J=1.74 Hz, 1H) 9.33 (t, J=1.56 Hz, 1H).

Workup

  1. customtransferred to a tared flask
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c899e1ac34504b408478e6a345cdc370
Source dataset
uspto-grants-2016_09
Patent number
US09446348B2

Linked notes

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