Imidazole → HCID 131719374, compound

HRID 1720334Notes

Reaction equation

HRID 1720334 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[Cl:10][C:11]1[CH:39]=[CH:38][CH:37]=[CH:36][C:12]=1[CH2:13][C:14]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:15]=1[C:16]1[C:17]([CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:18]([C:27]([OH:29])=[O:28])[N:19]=[CH:20][C:21]=1[NH:22]2>O1CCCC1>[N-:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:10][C:11]1[CH:39]=[CH:38][CH:37]=[CH:36][C:12]=1[CH2:13][C:14]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:15]=1[C:16]1[C:17]([CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:18]([C:27]([OH:29])=[O:28])[N:19]=[CH:20][C:21]=1[NH:22]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 131719375HCID 131719375, compound

Product 1

HCID 131719374HCID 131719374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1.5 g (0.0022 mol) of imidazole in 20 ml of tetrahydrofuran is mixed with 0.4 ml (0.0054 mol) of thionylchloride dissolved in 5 ml of tetrahydrofuran. The precipitate is suctioned off, the filtrate is instilled in a suspension of 0.693 g (0.00163 mol) of 5-(2-chlorobenzyl)-4-methoxyethoxymethyl-β-carboline-3-carboxylic acid in 30 ml of tetrahydrofuran. After it is left standing overnight the solvent is distilled off, the residue is dissolved in ethyl acetate, the solution is washed imidazole free with water. After concentration by evaporation 0.55 g (71% of theory) of 5-(2-chlorobenzyl)-4-methoxyethoxymethyl-β-carboline-3-carboxylic acid imidazolide remains.

Workup

  1. waitAfter it is left
  2. distillationthe solvent is distilled off
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washthe solution is washed imidazole free with water
  5. concentrationAfter concentration
  6. customby evaporation 0.55 g (71% of theory) of 5-(2-chlorobenzyl)-4-methoxyethoxymethyl-β-carboline-3-carboxylic acid imidazolide

Sources & evidence

ORD record
ord-2ce30014b33d4f6ba745a60833a314b0
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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