Acetic Acid → 1-Benzyl-2-methyl-5-(5-methyl-3-oxo-4,5-dihydro-2H-6-pyridazinyl)-benzimidazole

HRID 2199062Notes

Reaction equation

HRID 2199062 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([NH2:22])[CH:9]=2)=[N:6][NH:5][C:4](=[O:23])[CH2:3]1.N.[C:25](O)(=O)[CH3:26]>>[CH2:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:2]([CH3:1])[CH2:3][C:4](=[O:23])[NH:5][N:6]=3)=[CH:9][C:10]=2[N:22]=[C:25]1[CH3:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 131366765-Methyl-6-(3-amino-4-benzylamino-phenyl)-4,5-dihydro-2H-pyridazine-3-one

Product 1

HCID 205169121-Benzyl-2-methyl-5-(5-methyl-3-oxo-4,5-dihydro-2H-6-pyridazinyl)-benzimidazole

Procedure

The product obtained according to (a) was taken up in 100 ml of glacial acetic acid and refluxed for 2.5 hours. The mixture was mixed with ice and made alkaline with ammonia, and the precipitated product was purified by chromatography on silicagel (eluting agent: at first pure methylene chloride, then increasing amounts of acetone up to a mixture ratio methylene chloride/acetone=10:3). After evaporation, the product was obtained in crystalline form by trituration with ether.

Workup

  1. customThe product obtained
  2. temperaturerefluxed for 2.5 hours
  3. additionThe mixture was mixed with ice
  4. customthe precipitated product was purified by chromatography on silicagel (
  5. washeluting agent
  6. customAfter evaporation
  7. customthe product was obtained in crystalline form by trituration with ether

Sources & evidence

ORD record
ord-9ee450a4a9604427a0d8579d988df1bf
Source dataset
uspto-grants-1982_11
Patent number
US04361563

Reaction notes

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