Toluene → HCID 18931899, compound

HRID 1597726Notes

Reaction equation

HRID 1597726 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH2:22][CH3:23])[C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:33]=[O:34])C.P(Cl)(Cl)(Cl)=O.C1(C)C=CC=CC=1>[Cl-].[Zn+2].[Cl-].C1C=CC=CC=1.C(OCC)(=O)C>[C:24]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH2:22][CH3:23])[C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][C:17]([CH:33]=[O:34])=[CH:16][CH:15]=4)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 145496403-(2,2-Diphenylethenyl)-9-ethyl-9H-carbazole

Product 1

HCID 18931899HCID 18931899, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 21583983Benzene ethyl acetateSolvent

Procedure

35.4 g (87.87 mmol) of 3-(2',2'-diphenylvinyl)-9-ethylcarbazole (6a), 46.2 g (631.8 mmol) of DMF, 23.9 g (175.5 mmol) of zinc chloride, 80.7 g (526.6 mmol) of phosphorus oxychloride and 354 g of toluene were allowed to react and after treated in the same manner as with Example 1 (1). The crude product was treated by silica gel column chromatography (eluent; benzene/ethyl acetate=9/1 by volume), and recrystallized from a mixed solvent of toluene and heptane (3/2 by weight), thus obtaining 10.5 g of 3-(2',2'-diphenylvinyl)-6-formyl-9-ethylcarbazole.

Workup

  1. customto react
  2. customrecrystallized from a mixed solvent of toluene and heptane (3/2 by weight)

Sources & evidence

ORD record
ord-608507213d714688b2ee143a60ab5b7a
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

Loading…