Thionyl Chloride → HCID 178488083, compound

HRID 253477Notes

Reaction equation

HRID 253477 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[NH:7][C:8]([CH2:10]O)=[N:9][C:5]=2[CH:4]=1.S(Cl)([Cl:16])=O>ClCCl>[Cl:16][CH2:10][C:8]1[NH:7][C:6]2[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178488091HCID 178488091, compound

Product 1

HCID 178488083HCID 178488083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Methoxy-1H-benzoimidazol-2-yl)-methanol (221, 0.5 g, 3 mmol) was combined with 30 mL dichloromethane. Thionyl chloride (0.51 mL, 7 mmol) was added and the reaction was stirred at room temperature for 2 hours. The reaction was concentrated. Ethyl acetate was added and washed with sodium bicarbonate saturated solution and brine. The organic portion was dried over anhydrous sodium sulfate, filtered through Celite and evaporated to dryness. The resulting desired compound was used without further purification. MS (ESI) [M+H+]+=197.2.

Workup

  1. concentrationThe reaction was concentrated
  2. additionEthyl acetate was added
  3. washwashed with sodium bicarbonate saturated solution and brine
  4. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  5. filtrationfiltered through Celite
  6. customevaporated to dryness
  7. customThe resulting desired compound was used without further purification

Sources & evidence

ORD record
ord-efff9778628f49d1b04981788b941817
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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