Formic Acid → HCID 21468861, compound

HRID 976560Notes

Reaction equation

HRID 976560 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].[CH:17](O)=O>>[C:11]([C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[C:4]1[CH:5]=[CH:6][C:7]2[N:8]=[CH:17][NH:1][C:2]=2[CH:3]=1)#[N:12]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 21468845HCID 21468845, compound

Product 1

HCID 21468861HCID 21468861, compound

Procedure

2-(3,4-Diaminophenyl)benzonitrile (0.04 moles, 8.3 g) was refluxed in 100 ml formic acid for 3 hours. The solution was concentrated in vacuo, triturated with toluene, and dissolved in water. The pH of the solution was adjusted to 7.5 with 2N sodium hydroxide. The intermediate was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The solid was triturated with 25% ethyl acetate/75% hexane, filtered and purified by HPLC on silica gel eluted with a gradient of 50-75% ethyl acetate in hexane. The reaction yielded 7.3 g of 5-(2-Cyanophenyl)benzimidazole. (MS)

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customtriturated with toluene
  3. dissolutiondissolved in water
  4. extractionThe intermediate was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe solid was triturated with 25% ethyl acetate/75% hexane
  8. filtrationfiltered
  9. custompurified by HPLC on silica gel
  10. washeluted with a gradient of 50-75% ethyl acetate in hexane

Sources & evidence

ORD record
ord-dc3f219f33a54ba587be72a75f9b5033
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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