1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(4-chloro-phenyl)-7,8-dimethoxy-5-methyl-4H-1,3,4-triaza-phenalene

HRID 1351201Notes

Reaction equation

HRID 1351201 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:19]([CH2:20]I)[CH2:18][C:17]3[C:22]4[C:9]2=[N:10][CH:11]=[N:12][C:13]=4[CH:14]=[C:15]([O:25][CH3:26])[C:16]=3[O:23][CH3:24])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:19]([CH3:20])=[CH:18][C:17]3[C:22]4[C:9]2=[N:10][CH:11]=[N:12][C:13]=4[CH:14]=[C:15]([O:25][CH3:26])[C:16]=3[O:23][CH3:24])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 112370144-(4-chloro-phenyl)-5-iodomethyl-7,8-dimethoxy-5,6-dihydro-4H-1,3,4-triaza-phenalene

Product 1

HCID 114623424-(4-chloro-phenyl)-7,8-dimethoxy-5-methyl-4H-1,3,4-triaza-phenalene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(4-chloro-phenyl)-5-iodomethyl-7,8-dimethoxy-5,6-dihydro-4H-1,3,4-triaza-phenal (0.15 g, 0.31 mmol) (from Example 16, Step F, supra) in toluene (50 mL) was added DBU (0.46 mL, 3.1 mmol) (Fluka). The reaction mixture was heated at 120° C. for 1 hour. The mixture was then diluted with chloroform (100 mL), and washed with H2O. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:1:0.05) as eluent to give the desired 4-(4-chloro-phenyl)-7,8-dimethoxy-5-methyl-4H-1,3,4-triaza-phenalene as a pale yellow solid. (Yield 0.1 g, 91%).

Workup

  1. washwashed with H2O
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-fa1dce2a06c8430abe29b20fb42d71f1
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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