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

HRID 1925278Notes

Reaction equation

HRID 1925278 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-e9b02be0977d4745b9068175f2ee6f14
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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