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Potassium Iodide → (1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone

HRID 220783
Notes
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Reaction equation

HRID 220783 reaction equation
[H-].[Na+].[C:3]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([CH3:21])[NH:15][C:14]=2[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]1=2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[K+]>C1COCC1>[CH2:26]([N:15]1[C:14]2[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([C:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:10])[CH2:20][CH2:19][C:18]=2[N:17]=[C:16]1[CH3:21])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178432322HCID 178432322, compound

Product 1

HCID 57555380(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanoneYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in oil, 905 mg, 22.5 mmol) was placed in anhydrous THF (200 ml) and cooled down to 0° C. 6-Benzoyl-2-methyl-1,4,5,6-tetrahydro-1,3,6-triaza-benzo[e]azulene from Example E5.8 (4.9 g, 16.1 mmol) was added dropwise and the mixture was stirred for 1 h at room temperature. Benzyl bromide (2.31 ml, 19.3 mmol) and potassium iodide (1.34 g, 8.0 mmol) were added and the mixture was stirred for 16 h. The solution was diluted with EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (5.73 g, 90%).

Workup

  1. stirringthe mixture was stirred for 16 h
  2. additionThe solution was diluted with EtOAC
  3. washwashed with saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

Sources & evidence

ORD record
ord-3b2e528c7b67401f983f1b1af7ec7833
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes