Dimethylformamide → 3-[2-(Dimethylamino)ethoxy]-5-(trifluoromethyl)aniline

HRID 1994115Notes

Reaction equation

HRID 1994115 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+].CCCC[CH2:25][CH3:26].[CH3:27][N:28](C=O)[CH3:29]>CCOC(C)=O>[CH3:27][N:28]([CH3:29])[CH2:25][CH2:26][O:14][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=1)[NH2:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 10796Cesium carbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 210495493-[2-(Dimethylamino)ethoxy]-5-(trifluoromethyl)anilineYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-chloro-N1N-dimethylethanamine (0.355 g, 2.66 mmol), 3-nitro-5-(trifluoromethyl)phenol (0.500 g, 2.41 mmol) and Cs2CO3 (2.36 g, 7.24 mmol) in DMF (19 mL) was stirred at rt until reaction complete by TLC (1:1 EtOAc:Hexane). The mixture was diluted with EtOAc and washed with water. The organic solution was dried over Na2SO4, filtered, and concentrated to give the desired product as a brown oil (0.490 g, 63%). LCMS: (FA) ES+ 304.3 (M+1).

Workup

  1. washwashed with water
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0dd3becbc8694693b68732fb29c232fa
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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