Dinitrofluorobenzene → N-Benzyl-2,4-dinitroaniline

HRID 1494322Notes

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-1-fluorbenzen in 20 ml dry dimethylformamide was added dropwise, and the reaction mixture was stirred at 25° C. for 1 h. The mixture was evaporated, 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-de327e386cd34dfd99d635f241757547
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026704

Reaction notes

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