Imidazole → HCID 20523140, compound

HRID 223173Notes

Reaction equation

HRID 223173 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[O:13][CH:12]([CH2:17]N(C)C)[C:11]2=[O:21]>O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[O:13][CH:12]([CH2:17][C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)[C:11]2=[O:21]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 12327604HCID 12327604, compound

Product 1

HCID 20523140HCID 20523140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve imidazole (37.44 gms., 550 mmols) in water (200 ml.) and add 5-chloro-2-(dimethylaminomethyl)coumaran-3-one hydrochloride (25 gms., 55 mmols). Stir the reaction mixture overnight at room temperature, then add water (2 liters) and extract with chloroform (1 liter). Wash the chloroform solution with another 2 liter portion of water, dry over anhydrous magnesium sulfate, filter and evaporate in vacuo to give 5-chloro-2-(1'-imidazolylmethyl)coumaran-3-one.

Workup

  1. extractionadd water (2 liters) and extract with chloroform (1 liter)
  2. washWash the chloroform solution with another 2 liter portion of water
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-93684952cc2d4d1db2a2ee492d4f6f84
Source dataset
uspto-grants-1982_10
Patent number
US04352808

Reaction notes

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