Benzenamine, 4-methyl-N-(4-methylphenyl)- → 3-(N,N-di-p-tolylamino)-9H-carbazole

HRID 64536Notes

Reaction equation

C([N:4]1[C:16]2[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=O)C.[C:18]1([CH3:32])[CH:23]=[CH:22][C:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1>[Cu]=O>[C:28]1([CH3:31])[CH:29]=[CH:30][C:25]([N:24]([C:8]2[CH:7]=[CH:6][C:5]3[NH:4][C:16]4[C:11]([C:10]=3[CH:9]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:21]2[CH:20]=[CH:19][C:18]([CH3:32])=[CH:23][CH:22]=2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 1.2 g of 9-acetyl-3-bromocarbazole and 1.2 g of di-p-tolylamine were stirred together in 20 ml N,N′-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170° C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid was then taken up for further deprotection using 0.6 g KOH with THF (3 ml), methanol (6 ml) and water (6 ml) at reflux temperature. The reaction mixture was then extracted using ethyl acetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene/hexane (½) as eluent, yielded 1.2 g of 3-(N,N-di-p-tolylamino)-9H-carbazole.

Workup

customThe reaction was quenched with water
filtrationthe solid was filtered
washwashed with methanol
customdried under vacuum
temperatureat reflux temperature
extractionThe reaction mixture was then extracted
dry with materialand the organic layer was dried over anhydrous sodium sulfate
customevaporated to dryness under vacuum

Sources & evidence

ORD record: ord-d9803ac3404e454084e8800216b6305a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09450192B2

Reaction notes

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