Dimethylformamide → N-2-ethylhexyl-3,6-diformyl carbazole

HRID 983377Notes

Reaction equation

CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH3:11][CH2:12][N:13]1[C:25]2[C:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2.C(N1C2C=CC([CH:52]=[O:53])=CC=2C2C1=CC=C(C=O)C=2)CCCCCC>>[CH3:11][CH2:12][N:13]1[C:25]2[C:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][C:22]([CH:52]=[O:53])=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[C:17]([CH:4]=[O:5])[CH:18]=2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 11141782N-heptyl-3,6-Diformylcarbazole

HCID 66872719N-2-Ethylhexylcarbazole

Product 1

HCID 86590067N-2-ethylhexyl-3,6-diformyl carbazole

Procedure

N-2-ethylhexyl-3,6-diformyl carbazole was prepared from DMF (97 ml, 1.25 mol), POCl3 (116.5 ml, 1.25 mol), and N-2-ethylhexylcarbazole (50 g, 0.18 mol) according to the procedure described for N-heptyl-3,6-Diformylcarbazole. The product was obtained as 40 g of brownish liquid (66% yield). The product was used as is in the next step without any purification.

Sources & evidence

ORD record: ord-0b43e9d1255948f2ab0af6d383b895df
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864025B2

Reaction notes

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