Thionyl Chloride → N-(2-chloro-propyl)-benzimidazolone

HRID 127583Notes

Reaction equation

HRID 127583 reaction equation
O[CH:2]([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].O=S(Cl)[Cl:17]>O1CCOCC1>[Cl:17][CH:2]([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20240546HCID 20240546, compound

Product 1

HCID 20240547N-(2-chloro-propyl)-benzimidazolone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

13.2 gm of N-(2-hydroxy-propyl)-benzimidazolone were issolved in 150 ml of dioxane, and after addition of 8 ml of SOCl2 the mixture was refluxed for one hour. After evaporation in vacuo, the residue was dissolved in ethyl acetate, and the solution was washed with a sodium bicarbonate solution and water, and dried over Na2SO4. After distilling off the solvent, 13.4 gm of N-(2-chloro-propyl)-benzimidazolone were obtained.

Workup

  1. temperaturewas refluxed for one hour
  2. customAfter evaporation in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe solution was washed with a sodium bicarbonate solution and water
  5. dry with materialdried over Na2SO4
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-44f893b13d7148ffa3d7c162c04ae0c9
Source dataset
uspto-grants-1981_03
Patent number
US04256756

Reaction notes

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