Triethylamine → 5-Bromo-N,N-bis-(4-methoxy-benzyl)-N'-methyl-2-nitro-benzene-1,3-diamine

HRID 59933

Reaction equation

HRID 59933 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[Br:20][C:21]1[CH:22]=[C:23](F)[C:24]([N+:29]([O-:31])=[O:30])=[C:25]([CH:28]=1)[NH:26][CH3:27].CCN(CC)CC>CCOC(C)=O>[Br:20][C:21]1[CH:28]=[C:25]([NH:26][CH3:27])[C:24]([N+:29]([O-:31])=[O:30])=[C:23]([N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 716520385-Bromo-3-fluoro-N-methyl-2-nitroaniline

Product 1

HCID 1182353765-Bromo-N,N-bis-(4-methoxy-benzyl)-N'-methyl-2-nitro-benzene-1,3-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of bis-(4-methoxy-benzyl)-amine (346 mmol), 5-bromo-3-fluoro-N-methyl-2-nitroaniline (297 mmol) and Et3N (891 mmol) was stirred at 120° C. for 16 h. The mixture was then cooled. The crude was combined with another one obtained following the same procedure described above. The resulting mixture was diluted in EtOAc and washed (2×0.2 M HCl, H2O and sat. NaHCO3). The organic phase was dried (Na2SO4) and concentrated to afford the desired product.

Workup

  1. temperatureThe mixture was then cooled
  2. customobtained
  3. washwashed (2×0.2 M HCl, H2O and sat. NaHCO3)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77d2bf5a1eea489e882ac6cc015a40cc
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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