Thionyl Chloride → HCID 6423259, compound

HRID 623999Notes

Reaction equation

HRID 623999 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8]O)[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=1.S(Cl)([Cl:16])=O>C(Cl)Cl>[Cl:16][CH2:8][CH2:7][N:6]1[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7619262-(2-Methyl-1H-benzimidazol-1-yl)ethan-1-ol

Product 1

HCID 6423259HCID 6423259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-methyl-1H-benzoimidazol-1-yl)ethanol (4.00 g, 22.70 mmol) in DCM (80 mL) at 0° C., thionylchloride (3.5 mL, 48.25 mmol) was added. The reaction mixture was allowed to warm to rt and stirred for 5 h at this temperature, then the reaction mixture was quenched with aq. sat. NaHCO3-solution (gas evolution) and extracted with DCM (3×). The org. layers was dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 1-(2-chloroethyl)-2-methyl-1H-benzoimidazole which was used without further prufication in the next step. LC-MS conditions B: tR=0.37 min, [M+H]+=195.09.

Workup

  1. customthe reaction mixture was quenched with aq. sat. NaHCO3-solution (gas evolution)
  2. extractionextracted with DCM (3×)
  3. dry with materiallayers was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4895afd13e9145b49b2c9dff06782bd7
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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