Iodoethane → 2-chloro-1-ethyl-1H-1,3-benzodiazole

HRID 1886045Notes

Reaction equation

HRID 1886045 reaction equation
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[CH2:13](I)[CH3:14]>CN(C=O)C>[Cl:3][C:4]1[N:8]([CH2:13][CH3:14])[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 37447962-chloro-1-ethyl-1H-1,3-benzodiazoleYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) stirred suspension of NaH (60% dispersion in mineral oil; 7.08 g, 0.118 mol) in DMF (100 mL) was added 2-chlorobenzimidazole (15.00 g, 0.098 mol). The mixture was warmed to room temperature and stirred for 1 hour. Ethyl iodide (18.40 g, 0.118 mol) was added and stirring was continued for 3 hours. The mixture was poured onto the ice water and the resulting off-white solid was collected by filtration to give 10.0 g (61%) of product m.p. 48°-50° C.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 1 hour
  3. stirringstirring
  4. filtrationthe resulting off-white solid was collected by filtration

Sources & evidence

ORD record
ord-433eca85be8244e4bc52de6a8d0694dd
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

Loading…