1-Methylimidazole → HCID 178480909, compound

HRID 62546

Reaction equation

HRID 62546 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:7][CH2:8][CH:9]([OH:12])[CH2:10][OH:11]>CO>[Cl-:7].[OH:12][CH:9]([CH2:10][OH:11])[CH2:8][N+:4]1[CH:5]=[CH:6][N:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 72903-Chloro-1,2-propanediol

Product 1

HCID 178480909HCID 178480909, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methylimidazole (8.21 g, 100 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 (19.3 g, 100%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 3.19-3.29 (m, 1H) 3.36-3.48 (m, 1H) 3.77 (dd, J=6.78, 4.21 Hz, 1H) 3.87 (s, 3H) 4.10 (dd, J=13.74, 7.69 Hz, 1H) 4.32 (dd, J=13.74, 3.11 Hz, 1H) 5.13 (br. s., 1H) 5.53 (d, J=5.13 Hz, 1H) 7.72 (t, J=1.74 Hz, 1H) 7.74 (t, J=1.74 Hz, 1H) 9.18 (s, 1H).

Workup

  1. customtransferred to a tared flask
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-37cfc16f4f56478a95ee5ae1ce2d8544
Source dataset
uspto-grants-2016_09
Patent number
US09446348B2

Linked notes

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