Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 890912Notes

Reaction equation

[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[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([CH:30]=[O:31])C>>[C:14]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH:30]=[O:31])=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11775Triphenylamine

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-Yield 84%

Conditions

Temperature: 80 °C

Procedure

Triphenyl amine (98.32 g, 0.393 mol) is suspended in DMF (280 ml). Phosphorus oxychloride (66.24 g, 0.432 mol) is added dropwise to it over a 30-minutes period without external cooling. After stirring for one more hour, the reaction is heated to 80° C. (bath temperature) for 2½ hours. After cooling to room temperature, the reaction is slowly poured onto ice-cold water (8 liters) with vigorous stirring. After 30 minutes, aqueous sodium hydroxide (5 N, 250 ml) is added to the reaction, and stirring is continued for one hour. The obtained precipitate is filtered off, washed-with water (2 liters), then with methanol (2 litres) and dried to give 4-diphenylaminobenzaldehyde as a beige solid (90.47 g, 0.331 mol, 84%), which is used in the next step without further purification.

Workup

temperatureAfter cooling to room temperature
additionthe reaction is slowly poured onto ice-cold water (8 liters) with vigorous stirring
stirringstirring
waitis continued for one hour
filtrationThe obtained precipitate is filtered off, washed-with water (2 liters)
dry with materialwith methanol (2 litres) and dried

Sources & evidence

ORD record: ord-b2c66b5f1d40493c8910e2080ffe660b
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001677B2

Reaction notes

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