Ethylene Oxide → 4,5,6,7-Tetrabromo-1,3-dihydro-1,3-bis(2-hydroxyethyl)-2H-benzimidazol-2-one

HRID 1075976Notes

Reaction equation

HRID 1075976 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][C:8](=[O:11])[N:9]=2)[C:5]([Br:12])=[C:4]([Br:13])[C:3]=1[Br:14].[Cl-].[Li+].[CH2:17]1[O:19][CH2:18]1.[CH3:20][C:21](N(C)C)=[O:22]>>[OH:22][CH2:21][CH2:20][N:9]1[C:10]2[C:2]([Br:1])=[C:3]([Br:14])[C:4]([Br:13])=[C:5]([Br:12])[C:6]=2[N:7]([CH2:18][CH2:17][OH:19])[C:8]1=[O:11]

Participants

5

Reactant 4

HCID 6354Ethylene OxideHCID 31374Dimethylacetamide2×HCID 433294Lithium ChlorideHCID 16750062HCID 16750062, compound

Product 1

HCID 918004,5,6,7-Tetrabromo-1,3-dihydro-1,3-bis(2-hydroxyethyl)-2H-benzimidazol-2-one

Conditions

Temperature
80 °C

Procedure

44.96 g (0.1 mol) of 4,5,6,7-tetrabromobenzimidazolone are stirred with 250 ml of dimethylacetamide and 2.5 g of lithium chloride. A solution of 13.2 g of ethylene oxide (0.3 mol) in 100 ml of dimethylacetamide is added to this mixture at room temperature. The mixture is stirred slowly and heated to 80°C over the course of 2.5 hours. It is then stirred for a further 2 hours at 100°C. During the course of the reaction the starting material dissolves completely.

Workup

  1. stirringIt is then stirred for a further 2 hours at 100°C
  2. customDuring the course of the reaction the starting material
  3. dissolutiondissolves completely

Sources & evidence

ORD record
ord-48a53d99a26044479f864fdf2646e219
Source dataset
uspto-grants-1976_05
Patent number
US03954790

Reaction notes

Loading…