Dinitrofluorobenzene → N-Benzyl-2,4-dinitroaniline

HRID 1709198Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1F)([O-:18])=[O:17]>CN(C)C=O>[CH2:1]([NH:8][C:20]1[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2.68 g (25,0 mmol) benzylamine in 100 ml dry dimethylformamide was added 2.55 g (25.2 mmol) dry triethylamine. A solution of 4.65 g (25.0 mmol) 2,4-dinitro-1fluorbenzen in 20 ml dry dimethylformamide was added dropwise, and the reaction mixture was stirred at 25° C. for 1 h. The mixture was evaporated, and then dissolved in 50 ml ethylacetate and washed with 100 ml water. The ethyl acetate was evaporated to give 6.1 g (89 % ) N-benzyl-2,4- dinitroaniline. M.p. 106,2° C. 1H-NMR (CDCl3): 9.1 (1H, d), 8.9 (1H, broad s), 8.2 (1H, dd), 7.3 (5H,s), 6.9 (1H, d), 4.2 (2H, d).

Workup

customThe mixture was evaporated
dissolutiondissolved in 50 ml ethylacetate
washwashed with 100 ml water
customThe ethyl acetate was evaporated

Sources & evidence

ORD record: ord-744014e502b9472780f666137dbff077
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948794

Reaction notes

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