p-Xylyl bromide → (4-Methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine

HRID 51860

Reaction equation

HRID 51860 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].C(N([CH:19]([CH3:21])[CH3:20])C(C)C)C.[CH3:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:30][C:23]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:25][CH:24]=2)[CH2:22][C:23]2[CH:30]=[CH:29][C:26]([CH3:27])=[CH:25][CH:24]=2)=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 7721p-Xylyl bromideHCID 81531DiisopropylethylamineHCID 123071Benzenamine, 4-methoxy-3-nitro-

Product 1

HCID 22736971(4-Methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amineYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5.00 g (29.7 mmol) 4-methoxy-3-nitro-phenylamine in 60 ml acetonitrile at 0° C. were added 10.2 ml (59.5 mmol) N-ethyldiisopropylamine and 11.6 g (62.4 mmol) 4-methylbenzyl bromide. Stirring was continued at room temperature for 16 h and then the mixture was diluted with ethyl acetate and washed with 0.5 N hydrochloric acid and then with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford 10.4 g (93%) (4-methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine as an orange oil. ES-MS m/e (%): 399 (M+Na+, 18), 377 (M+H+, 100).

Workup

  1. washwashed with 0.5 N hydrochloric acid
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff2ffa8c03f24d1283bb8fd94dc8bf7e
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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