Acetic Acid → HCID 59214310, compound

HRID 552820Notes

Reaction equation

HRID 552820 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].CC(O)=O.[CH:15]([O-])([O-])[O:16][CH2:17][CH3:18]>>[CH2:17]([O:16][C:15]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[N:10]=1)[CH3:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7372853,4-DiaminobenzonitrileHCID 53630039Ethylorthoformate

Product 1

HCID 59214310HCID 59214310, compound

Conditions

Temperature
80 °C

Procedure

A solution of 3,4-diaminobenzonitrile (400 mg) in ethyl orthoformate (6.48 ml) was added AcOH (238 mg), followed by stirring at 80° C. for 2 hours. The reaction solution was cooled to room temperature, and partitioned between EtOAc and a 1M aqueous NaOH solution. The organic layer was washed with saturated brine, dried over anhydrous Na2SO3, and then collected by filtration, and the filtrate was concentrated, and purified by silica gel chromatography to obtain 2-ethoxy-1H-benzimidazole-6-carbonitrile (164 mg) as colorless powders.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. custompartitioned between EtOAc
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous Na2SO3
  5. filtrationcollected by filtration
  6. concentrationthe filtrate was concentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ce7ae922183e4db48e8e5d535f29868e
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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