Glycidol → HCID 21541435, compound

HRID 1075975Notes

Reaction equation

HRID 1075975 reaction equation
[N:1]1[C:2](=[O:10])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[Cl-].[Li+].[CH2:13]1[O:15][CH:14]1[CH2:16][OH:17]>CN(C)C(=O)C>[OH:15][CH:14]([CH2:16][OH:17])[CH2:13][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]([CH2:13][CH:14]([OH:15])[CH2:16][OH:17])[C:2]1=[O:10]

Participants

5

Reactant 3

HCID 11164GlycidolHCID 162542Benzimidazol-2-oneHCID 433294Lithium Chloride

Product 1

HCID 21541435HCID 21541435, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

1.5 mols of benzimidazolone (201.2 g) are dissolved in 1.5 liters of N,N-dimethylacetamide at 120°C and 2.5 g of lithium chloride are added. 244.2 g (3.3 mols) of glycerol glycide (glycidol) are added dropwise over the course of 2 hours to this solution. The solution is then stirred for a further 5 hours at 135°C. After bringing the solution to room temperature, it is filtered and completely concentrated. The residue is dried for a further 5 hours at 95°C under 0.8 mm Hg. This gives 448 g of a brownish, very viscous liquid (theoretical yield: 423.5 g) which is the crude product still contaminated with a little dimethylacetamide.

Workup

  1. customto room temperature
  2. filtrationit is filtered
  3. concentrationcompletely concentrated
  4. customThe residue is dried for a further 5 hours at 95°C under 0.8 mm Hg

Sources & evidence

ORD record
ord-36dd3069c3d343b98329f7ee839f1a59
Source dataset
uspto-grants-1976_05
Patent number
US03954790

Reaction notes

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