Acetic Anhydride → HCID 178432205, compound

HRID 552818Notes

Reaction equation

HRID 552818 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH3:11][C:12](OC(C)=O)=O>CC(O)=O>[CH3:11][C:12]1[NH:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178432205HCID 178432205, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3,4-diaminobenzonitrile (500 mg) in AcOH (10 ml) was added Ac2O (372 μl) at room temperature. The reaction mixture was refluxed for 15 hours (oil bath at 150° C.). It was cooled to room temperature, and concentrated until the amount of AcOH was reduced to a half. It was neutralized with an aqueous Na2CO3 solution, and extracted with EtOAc. The organic layer was washed with a saturated aqueous NaHCO3 solution and saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 2-methyl-1H-benzimidazole-5-carbonitrile (390 mg) as a pale red one.

Workup

  1. temperatureIt was cooled to room temperature
  2. concentrationconcentrated until the amount of AcOH
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with a saturated aqueous NaHCO3 solution and saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-314533dc390e441fb0499ab296f14a2c
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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