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Water → 6-(4-Nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

HRID 1353
Notes
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Reaction equation

HRID 1353 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:28]=[CH:27][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[NH:23][C:24]([CH3:26])=[N:25][C:15]=3[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:29]I.O>CN(C)C=O.C(Cl)(Cl)Cl>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[N:23]=[C:24]([CH3:26])[N:25]([CH3:29])[C:15]=3[CH2:14][CH2:13]2)=[O:11])=[CH:27][CH:28]=1)([O-:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418238HCID 178418238, compound

Product 1

HCID 699555616-(4-Nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6228DimethylformamideSolvent2×

Procedure

In a stream of argon, 144 mg of 60% sodium hydride was suspended in a small volume of N,N-dimethylformamide to which, with cooling on an ice bath, was then added dropwise a solution prepared by dissolving 500 mg of 6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine in 20 ml of N,N-dimethylformamide. After 1 hour of stirring at room temperature, the reaction solution was mixed with 0.11 ml of methyl iodide and stirred for 24 hours at room temperature. The reaction solution was mixed with water and chloroform, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography to obtain 351 mg of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine from the chloroform-methyl alcohol (30:1) eluate.

Workup

  1. temperaturewith cooling on an ice bath
  2. additionwas then added dropwise a solution
  3. customprepared
  4. stirringstirred for 24 hours at room temperature
  5. customthe resulting organic layer was separated
  6. washwashed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing the solvent
  9. distillationby distillation under a reduced pressure

Sources & evidence

ORD record
ord-a3bb18217e0f4155870b6f9c59379a87
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723606

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes