Water → HCID 18707484, compound

HRID 619355Notes

Reaction equation

HRID 619355 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:16]1([C:22]2[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[C:22]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:23]=[CH:24][C:25]([CH2:26][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 18707484HCID 18707484, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Carbazole (8.25 g, 49 mmol) was dissolved in N,N'-dimethylformamide (100 ml). Under a atmosphere of nitrogen was added sodium hydride (2.56 g, 64 mmol of a 60% suspension in mineral oil) in portion during 15 minutes. The mixture was then stirred at room temperature for 0.5 h. To the resulting mixture was added 4-phenylbenzylchloride (10 g, 49 mmol) in portions during 10 minutes. Then additional N,N'-dimethylformamide (100 ml) was added and the mixture was stirred at room temperature for 3.5 h. Water (125 ml) was added and the mixture was stirred vigorously at room temperature for 0.5 h, the solid formed was filtered off, washed with water (2×100 ml) and with hexane (2×100 ml). Drying in vacuo at 50° C. for 16 h afforded 15.9 g (97%) of 9-(biphenyl-4-ylmethyl)-9H-carbazole as a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 3.5 h
  2. stirringthe mixture was stirred vigorously at room temperature for 0.5 h
  3. customthe solid formed
  4. filtrationwas filtered off
  5. washwashed with water (2×100 ml) and with hexane (2×100 ml)
  6. customDrying in vacuo at 50° C. for 16 h

Sources & evidence

ORD record
ord-dc7f4c7e7631496c943297b9b4e03ba2
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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