HCID 57585829, compound → HCID 178475362, compound

HRID 547620Notes

Reaction equation

HRID 547620 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=O)=[C:7]([NH2:14])[CH:6]=1)(=[O:3])[CH3:2]>C(O)(=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]2[NH:11][CH:12]=[N:14][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 57585829HCID 57585829, compound

Product 1

HCID 178475362HCID 178475362, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Amino-4-(formylamino)phenyl acetate (10.3 g, 53.1 mmol) was dissolved in ˜100 mL of glacial acetic acid and heated at 65 degrees centigrade for approximately 18 hours. The reaction was concentrated and dried under vacuum. The residue was dissolved in ethyl acetate and washed three times with saturated NaHCO3. The organic layer was dried over MgSO4 and concentrated to give 6.89 g of 1H-benzimidazol-5-yl acetate. (M+1) 177.1, 1.02 min (LC/MS method B)

Workup

  1. temperatureheated at 65 degrees centigrade for approximately 18 hours
  2. concentrationThe reaction was concentrated
  3. customdried under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed three times with saturated NaHCO3
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed6d79c83ab34c1e848a6a76d46574b5
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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