Thionyl Chloride → HCID 20251885, compound

HRID 1284483Notes

Reaction equation

HRID 1284483 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]=1.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:22][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[N:6]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20251897HCID 20251897, compound

Product 1

HCID 20251885HCID 20251885, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-(3-hydroxypropyl)-1-phenyl-1H-benzimidazole (1.15 g) and thionyl chloride (0.6 g) in chloroform (23 ml) was refluxed for 1.5 hours. After being cooled, the mixture was diluted with a saturated aqueous solution of sodium bicarbonate. The chloroform layer was washed with water and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to afford 2-(3-chloropropyl)-1-phenyl-1H-benzimidazole (1.0 g).

Workup

  1. temperatureAfter being cooled
  2. washThe chloroform layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be907b50c7674320b032a63eb334185b
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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