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

HRID 74153

Reaction equation

HRID 74153 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+].[CH2:26]([NH2:28])[CH3:27].O>C(O)C>[CH2:26]([NH:28][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])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 11430Potassium CarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674983352-(4-Ethylamino-3-nitrophenyl)benzoxazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (321 mg, 2.32 mmol) and aqueous ethylamine solution (ca. 70%, 149 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 (310 mg, 94.3% 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-f2a56591e85a469080ab6dd762610ce5
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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