Water → HCID 18426794, compound

HRID 1281122Notes

Reaction equation

HRID 1281122 reaction equation
[C:1]([CH:3](O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)#[N:2].S(Cl)([Cl:24])=O.O>O1CCCC1>[Cl:24][CH:3]([C:1]#[N:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 18426803HCID 18426803, compound

Product 1

HCID 18426794HCID 18426794, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-[4-[cyano(hydroxy)methyl]phenyl]-5,6-dichlorobenzimidazole (275 mg, 0.865 mmol) in tetrahydrofuran (20 mL) was added thionyl chloride (0.38 mL, 5.2 mmol), and the mixture was heated to reflux for 3 h. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography (14:1 chloroform/acetonitrile) to afford of 2-[4-[chloro(cyano)methyl]phenyl]-5,6-dichlorobenzimidazole (73 mg, 25%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography (14:1 chloroform/acetonitrile)

Sources & evidence

ORD record
ord-93dd23c3cf7c43ac925fb60aa8cb3bce
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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