2-(Chloromethyl)-1H-imidazole hydrochloride → 2-[(Imidazole-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazole

HRID 2051774Notes

Reaction equation

HRID 2051774 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.Cl.Cl[CH2:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1>CN(C)C=O>[NH:19]1[CH:20]=[CH:21][N:22]=[C:18]1[CH2:17][S:14][C:2]1[NH:3][C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:8]=[CH:9][CH:10]=[CH:11]3

Participants

4

Reactant 2

HCID 27609292-(Chloromethyl)-1H-imidazole hydrochlorideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Product 1

HCID 202935502-[(Imidazole-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazoleYield 10.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of 1H-Naphth[2,3-d]imidazole-2-thiol and 0.8 g of 2-chloromethylimidazole-hydrochloride were heated for 11/2 hours at 90° in 20 ml of dimethylformamide. The precipitate formed was filtered off, washed with a small amount of acetonitrile, and dissolved in 2 N sodium bicarbonate solution. The aqueous phase was extracted three times with 30 ml of ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate, and then concentrated by evaporation. The residue was recrystallised from 150 ml of acetonitrile. 150 mg of 2-[(Imidazole-2-ylmethyl)thio]-1H-naphth[2,3-d]imidazole having a melting point of 172° was obtained.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with a small amount of acetonitrile
  4. dissolutiondissolved in 2 N sodium bicarbonate solution
  5. extractionThe aqueous phase was extracted three times with 30 ml of ethyl acetate
  6. washThe organic phases were washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated by evaporation
  9. customThe residue was recrystallised from 150 ml of acetonitrile

Sources & evidence

ORD record
ord-5923702e270b43918059080d28de82cc
Source dataset
uspto-grants-1980_01
Patent number
US04182766

Reaction notes

Loading…