Water → 2-(4-Isoproylamino-3-nitrophenyl)benzoxazole

HRID 74253Notes

Reaction equation

HRID 74253 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+].[CH:26]([NH2:29])([CH3:28])[CH3:27].O>C(O)C>[CH:26]([NH:29][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])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674980622-(4-Isoproylamino-3-nitrophenyl)benzoxazoleYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (200 mg, 0.774 mmol) in ethanol (5 mL) was added potassium carbonate (214 mg, 1.55 mmol) and isopropylamine (137 mg, 2.32 mmol), and this was heated to reflux for 4 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 (227 mg, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-a2f6c3f195c14ad9a52e22956408c4a6
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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