Dimethylformamide → 5-[N-(4-formylphenyl)-N-phenylamino]acenaphthene

HRID 1949

Reaction equation

[C:1]1([N:7]([C:14]2[C:24]3[C:25]4[C:17]([CH2:18][CH2:19][C:20]=4[CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:35]=[O:36]>O>[CH:35]([C:4]1[CH:3]=[CH:2][C:1]([N:7]([C:14]2[C:24]3[C:25]4[C:17]([CH2:18][CH2:19][C:20]=4[CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=1)=[O:36]

Participants

Conditions

Temperature: 50 °C

Procedure

32.14 g (0.1 mol) of the above prepared 5-(N,N-diphenylamino)acenaphthene was dissolved in 300 ml of N,N-dimethylformamide, and 22.73 g (0.15 mol) of phosphorus oxychloride was dropwise added thereto at room temperature for 30 minutes. After raising the temperature to 50° C., the reaction mixture was stirred for 14 hours. The reaction was determined to be finished when disappearance of 5-(N,N-diphenylamino)acenaphthene was identified. The reaction product was poured into an aqueous solution having 45 g (1.05 mol) of 93% sodium hydroxide dissolved in 1000 ml of water. The resultant mixture was cooled to precipitate a crystal, and the crystal was filtrated, washed with water and dried to obtain 30.27 g (yield: 86.6%, melting point: 138.0°-141.0° C.) of 5-[N-(4-formylphenyl)-N-phenylamino]acenaphthene.

Workup

additionThe reaction product was poured into an aqueous solution
customto precipitate a crystal
filtrationthe crystal was filtrated
washwashed with water
customdried

Sources & evidence

ORD record: ord-c9df1b4f59204cf6ba44f7f63a8372d9
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728500

Linked notes

Loading…