Acetic Anhydride → HCID 68129903, compound

HRID 1581146Notes

Reaction equation

HRID 1581146 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]3[NH:11][CH2:12][CH2:13][N:14]=3)[NH:8][C:4]=2[CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(O)C>[C:17]([NH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]3[NH:11][CH2:12][CH2:13][N:14]=3)[NH:8][C:4]=2[CH:3]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21561669HCID 21561669, compound

Product 1

HCID 68129903HCID 68129903, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(5-aminobenzimidazolyl) amino-2-imidazoline (0.48g, 0.0022 mol) and acetic anhydride (0.0022 mol) in ethanol (20 ml) was heated under reflux for 2 hours. The cooled reaction mixture was evaporated in vacuo and the resulting solid dissolved in methanol. Treatment with dry hydrogen chloride gas followed by ethyl acetate gave brown microcrystals (0.33 g). Recrystallisation from methanol/ethyl acetate gave a poor recovery of slightly hydroscopic 2-(5-acetylamino-2-benzimidazolyl) amino-2-imidazoline (50 mg) as colourless microcrystals m.p. 294°C (with shrinking). EXAMPLES 43 and 44

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe cooled reaction mixture
  4. customwas evaporated in vacuo
  5. dissolutionthe resulting solid dissolved in methanol
  6. customgave brown microcrystals (0.33 g)
  7. customRecrystallisation from methanol/ethyl acetate

Sources & evidence

ORD record
ord-5afab0af325c42cb9e32f5e0dbab77ee
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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