Acetone → HCID 14456402, compound

HRID 620037Notes

Reaction equation

HRID 620037 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([CH2:17][CH3:18])[C:14]([Cl:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:19]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.CC(C)=O>C(O)C>[ClH:16].[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([CH2:17][CH3:18])[C:14]([Cl:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:19][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 17274-AminopyridineHCID 14456400HCID 14456400, compound

Product 1

HCID 14456402HCID 14456402, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-phenyl-2-chloromethyl-5-chloro-6-ethylbenzimidazole (1.7 g, 5.5 mmol) prepared in the preceding step (b), 4-aminopyridine (1.8 g, 10.3 mmol) and ethanol (10.8 ml) was refluxed for 1.5 hours, then the mixture was filtered and the filtrate was concentrated in vacuo and crystallized from acetone (1.0 g, 2.35 mmol) and recrystallized from ethanol, then the objective compound (0.35 g, 0.82 mmol) was obtained.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3c31e67883b84319aa9bb05b0bbda463
Source dataset
uspto-grants-1989_04
Patent number
US04818761

Reaction notes

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