4-Fluoro-3-nitrobenzotrifluoride → N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenamine

HRID 2115785Notes

Reaction equation

HRID 2115785 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16]([CH3:22])[CH2:17][CH2:18][CH2:19][NH:20][CH3:21].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl>[CH3:15][N:16]([CH3:22])[CH2:17][CH2:18][CH2:19][N:20]([CH3:21])[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 16109008N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-fluoro-3-nitrobenzotrifluoride (1.00 g, 4.78 mmol) in THF (25 mL) was added N1,N1,N3-trimethylpropane-1,3-diamine (0.84 mL, 5.7 mmol) and NaHCO3 (1.1 g, 13 mmol). The resulting mixture was stirred for 1 h at RT, diluted with CH2Cl2, and washed with H2O. The organic layer was dried (MgSO4), filtered and concentrated to afford the title compound.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af48b1c0c41c42e9b05b859069f9e7bc
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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