Water → HCID 18426803, compound

HRID 1281121Notes

Reaction equation

HRID 1281121 reaction equation
[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.[C-:20]#[N:21].[K+].S([O-])(O)=O.[Na+].O>O1CCCC1>[C:20]([CH:15]([OH:16])[C:12]1[CH:11]=[CH:10][C:9]([C:7]2[NH:8][C:4]3[CH:3]=[C:2]([Cl:1])[C:18]([Cl:19])=[CH:17][C:5]=3[N:6]=2)=[CH:14][CH:13]=1)#[N:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 9032Potassium CyanideHCID 184267935,6-Dichloro-2-(4-formylphenyl)benzimidazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 18426803HCID 18426803, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-dichloro-2-(4-formylphenyl)benzimidazole (291 mg, 1.00 mmol) in tetrahydrofuran (40 mL) were added potassium cyanide (260 mg, 4.00 mmol), sodium hydrogen sulfite (500 mg), and water (10 mL). The mixture was stirred at room temperature for 12 h. 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 to afford 2-[4-[cyano(hydroxy)methyl]phenyl]-5,6-dichlorobenzimidazole (278 mg, 87%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0563bf97d40c47e2b5ebb4d8f879114a
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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