Thionyl Chloride → HCID 14722476, compound

HRID 1638559Notes

Reaction equation

HRID 1638559 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:24])=O>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][Cl:24])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 147224751-(4-Nitrobenzyl)-2-hydroxymethylbenzimidazole

Product 1

HCID 14722476HCID 14722476, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.2 g 1-(4-nitrobenzyl)-2-hydroxymethylbenzimidazole in 30 mL of chloroform was added 3.3 mL of thionyl chloride. The reaction mixture was stirred at room temperature for 18 hours and then concentrated in vacuo. The residue was taken up in water, neutralized with K2CO3 to a pH of 10 and extracted into methylene chloride. The organic layer was dried over Na2SO4 and concentrated to give 2 g of 1-(4-nitrobenzyl)-2-chloromethylbenzimidazole as a yellowish solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted into methylene chloride
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d06229224082413db601a69d10cbacb4
Source dataset
uspto-grants-1989_11
Patent number
US04880804

Reaction notes

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