Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 1363643Notes

Reaction equation

HRID 1363643 reaction equation
Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([CH:19]=[O:20])C>>[C:2]1([N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]2[CH:15]=[CH:14][C:13]([CH:19]=[O:20])=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-Yield 200%

Procedure

To a 300 ml four-neck flask were added 17.0 g (77 mmol) of 1,1-diphenylhydrazine hydrochloride obtained in Comparative Example 2, 21.1 g (77 mmol) of p-diphenylaminobenzaldehyde, and 70 g of DMF, followed by stirring at 40 to 45° C. for 3 hours. The reaction was traced by thin-layer chromatography. After, the completion of the reaction, 100 g of methanol was added and precipitated crystals were filtered off to obtain 32.3 g of p-diphenylaminobenzaldehyde=diphenylhydrazone. The yield was 95.4% based on the starting 1,1-diphenylhydrazine, the over all yield from the starting diphenylamine was 77.0%, and the purity determined by high-performance liquid chromatography was 98.2%.

Sources & evidence

ORD record
ord-427df1b4d7f440dc8d52b2412bea92ee
Source dataset
uspto-grants-2011_02
Patent number
US07884245B2

Reaction notes

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