Ammonium Chloride → 5-Bromo-N,N-bis-(4-methoxy-benzyl)-N''-methyl-benzene-1,2,3-triamine

HRID 59934Notes

Reaction equation

HRID 59934 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:30][CH3:31])[C:5]([N+:27]([O-])=O)=[C:6]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[NH4+].[Cl-].CO.C1COCC1>[Zn].C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:30][CH3:31])[C:5]([NH2:27])=[C:6]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21899815MeOH tetrahydrofuranHCID 1182353765-Bromo-N,N-bis-(4-methoxy-benzyl)-N'-methyl-2-nitro-benzene-1,3-diamine

Product 1

HCID 1182353785-Bromo-N,N-bis-(4-methoxy-benzyl)-N''-methyl-benzene-1,2,3-triamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 5-Bromo-N,N-bis-(4-methoxy-benzyl)-N′-methyl-2-nitro-benzene-1,3-diamine (170 mmol), NH4Cl (2038 mmol) and Zn (2034 mmol) in 1:1 MeOH/THF (1 L) was stirred at room temperature for 1 h. The mixture was cooled to 0° C. and HCOOH (20 mL) was added slowly. The mixture was allowed to reach room temperature and stirred for 1 h. The mixture was filtered and combined with another one obtained following the procedure described above. The resulting mixture was concentrated. The residue was dissolved in DCM. The organic mixture was washed (sat. NH4Cl), dried (Na2SO4) and concentrated to afford the desired product.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customto reach room temperature
  3. stirringstirred for 1 h
  4. filtrationThe mixture was filtered
  5. customobtained
  6. concentrationThe resulting mixture was concentrated
  7. dissolutionThe residue was dissolved in DCM
  8. washThe organic mixture was washed (sat. NH4Cl)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9fae7736eb804de590a966cb4d8f8bca
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

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