Methanol → HCID 90370245, compound

HRID 1755511Notes

Reaction equation

HRID 1755511 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[C:18]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:21]=[C:20]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:19]=1.CO>CN(C)C=O.O>[Cl:3][C:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:21]=[C:20]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:19]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 24758Sodium hydrideHCID 12532386HCID 12532386, compound

Product 1

HCID 90370245HCID 90370245, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent3×

Procedure

In a stream of nitrogen, a 100 mL three-necked flask was charged with 0.53 g (13.4 mmol) of sodium hydride (oily, 60%). 15 mL of dehydrated dimethylformamide was added to the content, and the mixture was stirred. To the thus-obtained slurry, a solution of 2.2 g (11.2 mmol) of 4-chlorocarbazole in 15 mL of dehydrated dimethylformamide was dropwise added, and the mixture was stirred for 30 minutes. To the thus-obtained reaction mixture, a solution of 3.0 g (11.2 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 40 mL of dehydrated dimethylformamide was dropwise added. The reaction mixture was stirred at room temperature for 2 hours, and, 10 mL of methanol and then 100 mL of pure water were added to terminate the reaction. A white powder deposited upon the addition of pure water was collected, and washed with pure water and then with ethanol. The thus-obtained powder was recrystallized from o-xylene to give 3.1 g (7.2 mmol) of 4-chloro-9-(4,6-diphenyl-1,3,5-triazin-2-yl)carbazole as a white crystal (yield: 64%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customTo the thus-obtained reaction mixture
  3. stirringThe reaction mixture was stirred at room temperature for 2 hours
  4. customto terminate
  5. customthe reaction
  6. customwas collected
  7. washwashed with pure water
  8. customThe thus-obtained powder was recrystallized from o-xylene

Sources & evidence

ORD record
ord-921f9538f170414c9dff4e0938eca9a8
Source dataset
uspto-grants-2015_10
Patent number
US09172045B2

Reaction notes

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