Acetic Anhydride → HCID 21561665, compound

HRID 1581144Notes

Reaction equation

HRID 1581144 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)[NH:9][C:5]=2[CH:4]=1.C(OC(=O)C)(=O)C>Br>[OH:2][C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)[NH:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21561670HCID 21561670, compound

Product 1

HCID 21561665HCID 21561665, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-(5-Methoxybenzimidazolyl)amino-2-imidazoline (prepared as described in Example 22 (2.55 g 0.011 mol) acetic anhydride (60 ml) and hydrogenbromide (48%) (50 ml) were heated under reflux for 4 hours. The mixture was cooled, evaporated under reduced pressure. The resulting sticky solid was dissolved in water and the filtered solution neutralised with sodium bicarbonate. This aqueous solution was extracted with ethyl acetate. The combined extracts were evaporated under reduced pressure to yield a light brown solid (0.87g) m.p. 254°-258°C. Recrystallisation from methanol gave a low recovery of 2-(5-hydroxybenzimidazolyl)amino-2-imidazoline monohydrate (0.16 g) as pale brown microcrystals m.p. 319°C (decomp.).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under reduced pressure
  5. dissolutionThe resulting sticky solid was dissolved in water
  6. extractionThis aqueous solution was extracted with ethyl acetate
  7. customThe combined extracts were evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e7231f430c84282909b70e48e579a76
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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