Sodium Carbonate → 1-(2'-Hexyldecyl)-2-ethyl-4,5,6,7-tetrahydrobenzimidazole

HRID 249222Notes

Reaction equation

HRID 249222 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1)[CH3:2].Br[CH2:13][CH:14]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[CH2:23]([CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][N:7]1[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[N:4]=[C:3]1[CH2:1][CH3:2])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 18459580Pentadecane, 7-(bromomethyl)-HCID 189979322-Ethyl-4,5,6,7-tetrahydrobenzimidazole

Product 1

HCID 189979291-(2'-Hexyldecyl)-2-ethyl-4,5,6,7-tetrahydrobenzimidazole

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

2-Ethyl-4,5,6,7-tetrahydrobenzimidazole (14.3 parts), 2-methoxyethanol (30 parts), 1-bromo-2-hexyldecane (35 parts) and sodium carbonate (5.7 parts) are stirred together and heated at 125°-135° C. below a reflux condenser for 15 hours. The reaction mixture is cooled and extracted with a mixture of toluene (150 parts) and ethyl acetate (50 parts) and the extract is washed successively with water, dilute sulphuric acid, dilute sodium hydroxide, and water, and then distilled yielding 1-(2'-hexyldecyl)-2-ethyl-4,5,6,7-tetrahydrobenzimidazole (V) (16.6 parts), b.p. 185°-200° at 0.2 mm pressure.

Workup

  1. temperatureheated at 125°-135° C. below a reflux condenser for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with a mixture of toluene (150 parts) and ethyl acetate (50 parts)
  4. washthe extract is washed successively with water, dilute sulphuric acid, dilute sodium hydroxide, and water
  5. distillationdistilled

Sources & evidence

ORD record
ord-e455e2f537164ad0883c7d0302fc97e0
Source dataset
uspto-grants-1993_05
Patent number
US05213777

Reaction notes

Loading…