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

HRID 62550

Reaction equation

HRID 62550 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cl:10][CH2:11][CH:12]([OH:15])[CH2:13][OH:14]>CO>[Cl-:10].[OH:15][CH:12]([CH2:13][OH:14])[CH2:11][N+:7]1[CH:8]=[CH:9][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1

Participants

4

Reactant 2

HCID 72903-Chloro-1,2-propanediolHCID 61347Butylimidazole

Product 1

HCID 866682691-(2,3-Dihydroxypropyl)-3-butylimidazolium ChlorideYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Butylimidazole (12.42 g, 100.0 mmol) and 3-chloro-1,2-propanediol (11.05 g, 100.0 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 (23.27 g, 92%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 0.89 (t, 3H) 1.17-1.31 (m, 2H) 1.69-1.83 (m, 2H) 3.19-3.28 (m, 1H) 3.37-3.46 (m, 1H) 3.78 (dd, J=7.05, 4.49 Hz, 1H) 4.12 (dd, J=13.83, 7.60 Hz, 1H) 4.20 (t, J=7.14 Hz, 2H) 4.33 (dd, J=13.74, 3.11 Hz, 1H) 5.16 (br. s., 1H) 5.56 (d, J=5.31 Hz, 1H) 7.78 (t, J=1.74 Hz, 1H) 7.83 (t, J=1.74 Hz, 1H) 9.30 (t, J=1.47 Hz, 1H).

Workup

  1. customtransferred to a tared flask
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8bb2ea9498f7445c8bff7b76e57715ea
Source dataset
uspto-grants-2016_09
Patent number
US09446348B2

Linked notes

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