Water → N-(2-dimethylaminoethyl)-4-(benzoxazol-2-yl)-2-nitroaniline

HRID 74311Notes

Reaction equation

HRID 74311 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30].O>C(#N)C>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH:30][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 67498833N-(2-dimethylaminoethyl)-4-(benzoxazol-2-yl)-2-nitroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (200 mg, 0.775 mmol) in acetonitrile (5 mL) was added potassium carbonate (214 mg, 1.55 mmol) and N,N-dimethylethylenediamine (82 mg, 0.93 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, this was cooled to room temperature, water was added, and after the precipitated crystals were filtered and washed with water, they were dried to yield the title compound (240 mg, 95% yield) as orange crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. filtrationafter the precipitated crystals were filtered
  4. washwashed with water, they
  5. customwere dried

Sources & evidence

ORD record
ord-f0548328b9ba49da8773e3c330c166e1
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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