2-Chloromethylbenzimidazole → HCID 23205615, compound

HRID 962488Notes

Reaction equation

HRID 962488 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][NH:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1.[CH2:31](O)[CH3:32].O.Cl[CH2:36][C:37]1[NH:38][C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=1>C(O)C>[NH:41]1[C:40]2[CH:42]=[CH:43][CH:44]=[CH:45][C:39]=2[N:38]=[C:37]1[CH2:36][N:10]([CH2:11][C:12]1[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH2:9][CH2:8][N:7]([CH2:36][C:37]1[NH:38][C:39]2[CH:40]=[CH:42][CH:43]=[CH:31][C:32]=2[N:41]=1)[CH2:6][C:5]1[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 785712-ChloromethylbenzimidazoleHCID 11133569HCID 11133569, compoundHCID 19096565Water ethanol

Product 1

HCID 23205615HCID 23205615, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

1.5 g N,N'-bis-(3,4,5-trimethoxybenzyl) ethylenediamine dichlorhydrate were solubilized in 30 ml 1:1 ethanol/water mixture. The pH of the solution was brought to 11 using a soda solution. A solution of 1.1 g 2-chloromethyl benzimidazole in solution in 30 ml ethanol was added all at once. The mixture was heated for 5 hours at 45° C. while keeping the pH at between 10 and 11 by adding a soda solution. After cooling, the ethanol was evaporated in a vacuum, and the medium was cooled to 0° C. The precipitate formed was filtered and washed with water. The solid was taken up in 15 ml water +0.5 ml concentrated HCl, then filtered and washed in water. The solid was then recrystallized in 10 ml of a 98:2 water/ethanol mixture. 350 mg of a white powder having a melting point of 150° C. (dec.) were obtained, whose proton NMR spectrum (400 MHZ) and ultimate analysis matched the expected structure (in the form of dichlorhydrate).

Workup

  1. additionby adding a soda solution
  2. temperatureAfter cooling
  3. customthe ethanol was evaporated in a vacuum
  4. temperaturethe medium was cooled to 0° C
  5. customThe precipitate formed
  6. filtrationwas filtered
  7. washwashed with water
  8. filtrationfiltered
  9. washwashed in water
  10. customThe solid was then recrystallized in 10 ml of a 98:2 water/ethanol mixture
  11. customwere obtained

Sources & evidence

ORD record
ord-4916c88f88ef427a87fa8a0b4b7a6f4f
Source dataset
uspto-grants-1998_06
Patent number
US05760037

Reaction notes

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