4-Aminopyridine → HCID 70381943, compound

HRID 986663Notes

Reaction equation

HRID 986663 reaction equation
[Cl:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1>C(O)C>[ClH:1].[ClH:1].[N:16]1[CH:17]=[CH:18][C:13]([NH:12][CH2:2][C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 70381943HCID 70381943, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.665 g (10 m mol) of 2- chloromethybenzimidazole and 1.88 g (20 m mol) of 4- aminopyridine in 20 ml of ethanol was refluxed under heating for three hours. The solution was evaporated in vacuo to a dark oil, dissolved in 20 ml of water and washed twice with 20 ml of ethylacetate The aqueous phase was evaporated in vacuo. The residual oil was dissolved in 3 ml of concentrated hydrochloric acid and chilled (0° C.) causing a crystalline precipitate to form. The crystals were filtered with the aid of ethanol. Recrystallization from methanol gave 1.68 g (53.3%) of the title compound (I).

Workup

  1. temperatureunder heating for three hours
  2. customThe solution was evaporated in vacuo to a dark oil
  3. dissolutiondissolved in 20 ml of water
  4. washwashed twice with 20 ml of ethylacetate The aqueous phase
  5. customwas evaporated in vacuo
  6. dissolutionThe residual oil was dissolved in 3 ml of concentrated hydrochloric acid
  7. customto form
  8. filtrationThe crystals were filtered with the aid of ethanol
  9. customRecrystallization from methanol

Sources & evidence

ORD record
ord-07c970f2191141729624b113c9814452
Source dataset
uspto-grants-1987_12
Patent number
US04714764

Reaction notes

Loading…