Formanilide → 4-Nitrodiphenylamine

HRID 127815

Reaction equation

HRID 127815 reaction equation
C([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[H-].[Na+].[Na].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1C(F)(F)F>CN(C)C=O>[CH:7]1[CH:8]=[CH:9][C:4]([NH:3][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 7671FormanilideHCID 24758Sodium hydrideHCID 612132-Chloro-5-nitrobenzotrifluorideHCID 5360545Sodium

Product 1

HCID 132714-Nitrodiphenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

the formanilide is treated with a one-molar equivalent of sodium hydride in dimethylformamide and the resulting solution of the sodium salt is treated with 2-chloro-5-nitrobenzotrifluoride (U.S. Pat. No. 3,657,350) at an elevated temperature (e.g., 155° C., reflux), to give the 4-nitrodiphenylamine (J. Organic Chemistry, 42, 1786 (1977) and references therein).

Sources & evidence

ORD record
ord-637345e1568f43cdb0c527fe3b2389c2
Source dataset
uspto-grants-1981_03
Patent number
US04257805

Linked notes

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