Ethyl Acetate → HCID 178509648, compound

HRID 743906Notes

Reaction equation

HRID 743906 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[NH2:8].C(O[CH2:21][CH3:22])(=O)C>C(O)C.[Cl-].[Na+].O>[CH2:21]([C:22]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[CH:3][C:2]=2[N:1]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 21468845HCID 21468845, compound

Product 1

HCID 178509648HCID 178509648, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(3,4-Diaminophenyl)benzonitrile (2.4 mmoles, 0.50 g) was dissolved in 3 ml ethanol. Ethyl phenylacetamidate hydrochloride (2.88 mmoles, 0.573 g) (prepared from HCl gas bubbled through benzyl cyanide and ethanol) was added. The reaction was warmed on a steam bath for 10 minutes. Ethyl acetate and brine were added. The organic phase was separated dried and concentrated. The product was precipitated from ethyl acetate and hexane and filtered to yield 290 mg of 2-benzyl-5-(2-cyanophenyl)-1H-benzimidazole. (MS)

Workup

  1. temperatureThe reaction was warmed on a steam bath for 10 minutes
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe product was precipitated from ethyl acetate and hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7015f33cfa03437a91670234c840e825
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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