Thionyl Chloride → HCID 55029240, compound

HRID 1500840Notes

Reaction equation

HRID 1500840 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16]O)(=[O:4])=[O:3].O=S(Cl)[Cl:20]>C(Cl)Cl>[Cl:20][CH2:16][C:8]1[N:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 47159112HCID 47159112, compound

Product 1

HCID 55029240HCID 55029240, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude (1-(2-(methylsulfonyl)ethyl)-1H-benzo[d]imidazol-2-yl)methanol in DCM (30 mL) was added SOCl2 (5 mL). The mixture was heated to reflux and monitored by LCMS. After the reaction completed, the solvents was evaporated. The residue was redissolved in DCM (100 mL) and washed with saturated NaHCO3 (2×30 mL), dried over Na2SO4 and concentrated under vacuum to afford the crude product (600 mg, yield: 33%) as oil. MS obsd. (ESI+) [(M+H)+]: 273.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe solvents was evaporated
  4. dissolutionThe residue was redissolved in DCM (100 mL)
  5. washwashed with saturated NaHCO3 (2×30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-404193c9f63e439eae092f0b00ba8f9c
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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