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

HRID 62549

Reaction equation

HRID 62549 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)[CH2:2][CH3:3].[Cl:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13]>CO>[Cl-:9].[OH:14][CH:11]([CH2:12][OH:13])[CH2:10][N+:6]1[CH:7]=[CH:8][N:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1

Participants

4

Reactant 2

HCID 72903-Chloro-1,2-propanediolHCID 118785n-Propylimidazole

Product 1

HCID 866682671-(2,3-Dihydroxypropyl)-3-propylimidazolium ChlorideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Propylimidazole (2.75 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 (5.20 g, 95%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 0.84 (t, J=7.42 Hz, 3H) 1.74-1.86 (m, 2H) 3.22 (dd, J=11.17, 6.96 Hz, 1H) 3.42 (dd, J=10.99, 4.95 Hz, 1H) 4.07-4.20 (m, 3H) 4.33 (dd, J=13.74, 3.11 Hz, 1H) 5.15 (br. s., 1H) 5.56 (br. s., 1H) 7.78 (t, J=1.74 Hz, 1H) 7.82 (t, J=1.83 Hz, 1H) 9.29 (t, J=1.47 Hz, 1H).

Workup

  1. customtransferred to a tared flask
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9b9aef82645c46caa57ddd348bdffbc0
Source dataset
uspto-grants-2016_09
Patent number
US09446348B2

Linked notes

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