Imidazole → HCID 15093123, compound

HRID 359000Notes

Reaction equation

HRID 359000 reaction equation
Cl[CH2:2][C:3]([NH:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:20][C:7]1=2)=[O:4].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>C1(C)C=CC=CC=1>[N:25]1([CH2:2][C:3]([NH:5][CH:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][O:9][C:8]3[CH:17]=[CH:18][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:20][C:7]2=3)=[O:4])[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 19088555HCID 19088555, compound

Product 1

HCID 15093123HCID 15093123, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Crude methyl 11-chloroacetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate, 3.0 g, was heated to reflux for 4 hours in 100 ml of toluene together with 0.9 g of imidazole. After allowing to cool, the solvent was distilled off under reduced pressure. The obtained residue was extracted with 300 ml of methylene chloride. The extract was washed successively with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=10:1) to give 1.6 g of the product.

Workup

  1. temperatureto cool
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionThe obtained residue was extracted with 300 ml of methylene chloride
  4. washThe extract was washed successively with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a842d9e52ed6424ba66483cdc118e58c
Source dataset
uspto-grants-1991_03
Patent number
US04999363

Reaction notes

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